Oxidative Umpolung α‑Alkylation of Ketones
We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl...
Saved in:
| Published in | Organic letters Vol. 17; no. 2; pp. 282 - 285 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
16.01.2015
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies. |
|---|---|
| AbstractList | We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies. We disclose a hypervalent iodine mediated zeta-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The alpha-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies. |
| Author | Shneider, O. Svetlana Pisarevsky, Evgeni Fristrup, Peter Szpilman, Alex M |
| AuthorAffiliation | Department of Chemistry Technion-Israel Institute of Technology Technical University of Denmark Schulich Faculty of Chemistry |
| AuthorAffiliation_xml | – name: Schulich Faculty of Chemistry – name: Department of Chemistry – name: Technical University of Denmark – name: Technion-Israel Institute of Technology |
| Author_xml | – sequence: 1 givenname: O. Svetlana surname: Shneider fullname: Shneider, O. Svetlana – sequence: 2 givenname: Evgeni surname: Pisarevsky fullname: Pisarevsky, Evgeni – sequence: 3 givenname: Peter surname: Fristrup fullname: Fristrup, Peter – sequence: 4 givenname: Alex M surname: Szpilman fullname: Szpilman, Alex M email: Szpilman@tx.technion.ac.il |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25562460$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkEtOwzAQQC1URD-w4AIoGyQQCozt2DjLquInkLqh68h1HJSS2CVOgO64AkfhIhyCk-CSkhULNvbI82Y884aoZ6zRCO1jOMVA8JktGFAqIrWFBpgRGp4DI70u5tBHQ-cWANi_xDuoTxjjJOIwQOH0NU9lnT_rYFYubdGYh-Dz4-vtfVw8rgqfsCawWXCra_-l20XbmSyc3tvcIzS7vLifXId306ubyfgulBSzOsQ4Y0REQOcpB8p1jLmCNI6lEowJSSFigmINDEDqOI0kZFzjjIjUb5H6Y4SO2r7Lyj412tVJmTuli0IabRuXYO43E4RGa_S4RVVlnat0liyrvJTVKsGQrO0knR3PHmzaNvNSpx35q8MDJy3wouc2cyrXRukOAwAaCUqx8BGJPS3-T0_y-sfmxDam9qWHbalULlnYpjJe5x8TfwN6x40I |
| CitedBy_id | crossref_primary_10_1002_ange_201610274 crossref_primary_10_1002_anie_202005286 crossref_primary_10_1021_jacs_6b05344 crossref_primary_10_1002_ajoc_201700256 crossref_primary_10_1002_anie_201701538 crossref_primary_10_3389_fchem_2020_00467 crossref_primary_10_1021_acs_cgd_9b00116 crossref_primary_10_1002_tcr_202100172 crossref_primary_10_1021_acs_orglett_9b03824 crossref_primary_10_1039_C9SC03663F crossref_primary_10_1021_acs_joc_2c00054 crossref_primary_10_2174_0113852728302831240315064301 crossref_primary_10_1002_ajoc_202100194 crossref_primary_10_1002_anie_201703641 crossref_primary_10_1021_acs_orglett_5b01836 crossref_primary_10_1039_C9OB01267B crossref_primary_10_1002_tcr_201500017 crossref_primary_10_1039_C6RA00653A crossref_primary_10_1039_D3OB00083D crossref_primary_10_1002_ange_202210317 crossref_primary_10_1002_anie_201610274 crossref_primary_10_1021_acs_joc_1c01517 crossref_primary_10_1021_acs_orglett_6b00310 crossref_primary_10_1002_ange_202005286 crossref_primary_10_1021_acs_joc_0c02868 crossref_primary_10_1021_jacs_7b08813 crossref_primary_10_1021_acscatal_7b00975 crossref_primary_10_1002_ajoc_201800632 crossref_primary_10_1002_chin_201523060 crossref_primary_10_1002_anie_202007439 crossref_primary_10_1002_chem_201501177 crossref_primary_10_1007_s11426_016_0478_3 crossref_primary_10_1039_C4OB02601B crossref_primary_10_1039_D1QO00346A crossref_primary_10_1126_science_abq3048 crossref_primary_10_1002_ange_201701538 crossref_primary_10_1021_acs_joc_7b03058 crossref_primary_10_1021_acs_joc_2c02125 crossref_primary_10_1002_ange_202007439 crossref_primary_10_1021_acs_orglett_9b00422 crossref_primary_10_1002_ange_201703641 crossref_primary_10_1016_j_ica_2016_08_009 crossref_primary_10_1021_acs_orglett_3c00313 crossref_primary_10_1038_s41467_019_13175_5 crossref_primary_10_1002_anie_202210317 crossref_primary_10_1039_D0SC03266B crossref_primary_10_1002_aoc_6390 crossref_primary_10_1021_acs_orglett_7b03064 |
| Cites_doi | 10.1021/ol801574m 10.1002/chem.201300860 10.1021/cr100379j 10.1021/ja2008906 10.1021/ja408296h 10.1002/cctc.201300774 10.1021/cr300475r 10.1002/chem.200501052 10.1002/anie.201004374 10.1002/anie.200603497 10.1002/anie.201309270 10.1021/ja206050b 10.1002/anie.201203704 10.1021/jm000170m 10.1002/anie.201201653 10.1002/chem.201001539 10.3998/ark.5550190.0014.207 10.1002/adsc.201300266 10.1039/b004265j 10.1002/chem.201001110 10.1002/anie.201400405 10.1021/cr000411y 10.1073/pnas.1002845107 10.1055/s-0033-1339192 10.1021/ja100748y 10.1039/c2cs15333e 10.1021/ja303116v 10.1021/jo100796s 10.1021/cr800332c 10.1021/ja804159y 10.1016/S0040-4039(01)90297-7 10.1016/S0040-4039(00)87051-3 10.1055/s-1990-21097 10.1021/jo00196a024 10.1002/chem.19950010508 10.1002/1099-0690(20021)2002:1<181::AID-EJOC181>3.0.CO;2-3 10.1021/jo00272a028 10.1021/jo00890a018 10.1002/ange.201004374 10.1016/0022-328X(90)85039-2 10.1021/jo00133a053 10.1021/ol005843+ 10.1016/B978-0-08-097742-3.00735-7 |
| ContentType | Journal Article |
| Copyright | Copyright © 2015 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2015 American Chemical Society |
| DBID | 1KM 1KN BLEPL DTL GVOUP NPM AAYXX CITATION 7X8 |
| DOI | 10.1021/ol503384c |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2015 PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | Web of Science PubMed CrossRef MEDLINE - Academic |
| DatabaseTitleList | PubMed Web of Science MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1523-7052 |
| EndPage | 285 |
| ExternalDocumentID | 10_1021_ol503384c 25562460 000348331800029 d214306790 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: Israel Science Foundation grantid: 1419/10 |
| GroupedDBID | - .K2 123 4.4 53G 55A 5VS 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 DZ EBS ED ED~ F5P GNL IH9 IHE JG JG~ K2 LG6 P2P RNS ROL TN5 UI2 VF5 VG9 W1F X YNT --- -DZ -~X 1KM 1KN 6P2 AAHBH ABJNI ABQRX ADHLV AHGAQ BLEPL CUPRZ DTL GGK GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED NPM AAYXX CITATION 7X8 |
| ID | FETCH-LOGICAL-a315t-11f528403bd6036e916c0d99ac8558a3045831e0500ae9d4a0f6e1f28d338dd33 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 44 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000348331800029 |
| ISSN | 1523-7060 |
| IngestDate | Fri Aug 16 23:35:52 EDT 2024 Fri Aug 23 01:50:47 EDT 2024 Sat Sep 28 07:57:06 EDT 2024 Tue Aug 27 15:36:48 EDT 2024 Fri Nov 01 20:17:21 EDT 2024 Thu Aug 27 13:41:59 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 2 |
| Keywords | CATALYSIS ALKENES ARYLATION TOSYLOXYLATION CHEMISTRY SALTS TRIFLUOROMETHYLATION |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a315t-11f528403bd6036e916c0d99ac8558a3045831e0500ae9d4a0f6e1f28d338dd33 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0001-7790-4129 0000-0001-7175-3796 |
| PMID | 25562460 |
| PQID | 1652382343 |
| PQPubID | 23479 |
| PageCount | 4 |
| ParticipantIDs | webofscience_primary_000348331800029CitationCount crossref_primary_10_1021_ol503384c webofscience_primary_000348331800029 pubmed_primary_25562460 acs_journals_10_1021_ol503384c proquest_miscellaneous_1652382343 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
| PublicationCentury | 2000 |
| PublicationDate | 20150116 2015-01-16 2015-Jan-16 |
| PublicationDateYYYYMMDD | 2015-01-16 |
| PublicationDate_xml | – month: 01 year: 2015 text: 20150116 day: 16 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Organic letters |
| PublicationTitleAbbrev | ORG LETT |
| PublicationTitleAlternate | Org. Lett |
| PublicationYear | 2015 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | UMEMOTO, T (WOS:A1987K702300066) 1987; 60 Eisenberger, P (WOS:000236257800020) 2006; 12 Skucas, E (WOS:000304837800018) 2012; 134 ZHDANKIN, VV (WOS:A1989U852000028) 1989; 54 Harvey, JS (WOS:000295241400005) 2011; 133 Molander, G. A. (000348331800029.35) 2014; 7 Neilands, O. (000348331800029.29) 1965; 1 Gonzalez, DF (WOS:000319420200026) 2013; 355 UMEMOTO, T (WOS:A1982NG71900011) 1982; 23 Stauffer, SR (WOS:000166045700004) 2000; 43 Lee, K (WOS:000304814000042) 2012; 51 BOLM, C (WOS:A1995RX52500005) 1995; 1 DeMartino, MP (WOS:000258660600055) 2008; 130 KOSER, GF (WOS:A1982NS61000053) 1982; 47 Kieltsch, I (WOS:000243855500019) 2007; 46 (000348331800029.1) 2013 ADAMCZYK, M (WOS:A1984TR09700024) 1984; 49 Winfield, CJ (WOS:000089855200014) 2000 Malmgren, J (WOS:000321983700034) 2013; 19 MORIARTY, RM (WOS:A1990DN41500001) 1990 Miyata, O (WOS:000324460900007) 2013 Takeda, T (WOS:000326125200010) 2013; 135 Izquierdo, J (WOS:000311702000006) 2012; 51 SEEBACH, D (WOS:A1975V343800018) 1975; 40 Mizar, P (WOS:000337094200048) 2014; 53 Pu, L (WOS:000167639400005) 2001; 101 Tzirakis, MD (WOS:000321810600017) 2013; 113 Zhdankin, VV (WOS:000261723400011) 2008; 108 He, ZH (WOS:000279030900041) 2010; 75 Eames, J (WOS:000173118500022) 2002; 2002 van der Deen, H (WOS:000087292600025) 2000; 2 Zhdankin, V. V. (000348331800029.45) 2014 VANDERSTEEN, FH (WOS:A1990DQ86100015) 1990; 390 Guo, WS (WOS:000337637100010) 2014; 6 Rovis, T (WOS:000320576300003) 2013; 24 Chen, MZ (WOS:000336504500012) 2014; 53 MORIARTY, RM (WOS:A1981LG72400001) 1981; 22 Gonzalez, DF (WOS:000281539500016) 2010; 16 Fernandez-Ibanez, MA (WOS:000259197600028) 2008; 10 Miyoshi, T (WOS:000287157600025) 2011; 50 Bugaut, X (WOS:000302559700005) 2012; 41 Neilands, O. (000348331800029.30) 1966; 2 Norrby, PO (WOS:000280819100003) 2010; 16 Allen, AE (WOS:000291715300030) 2011; 133 Liu, C (WOS:000288820600015) 2011; 111 Allen, AE (WOS:000276553700007) 2010; 132 Mastracchio, A (WOS:000284762400015) 2010; 107 ref17/cit17b Miyoshi T. (ref4/cit4) 2011; 123 Norrby P.-O. (ref7/cit7) 2010; 16 Zhdankin V. V. (ref5/cit5a) 2014 Neilands O. (ref22/cit22b) 1966; 2 Pu L. (ref16/cit16) 2001; 101 Fernández-Ibáňez M. Á. (ref24/cit24b) 2008; 10 Bugaut X. (ref3/cit3a) 2012; 41 Eames J. (ref20/cit20b) 2002 DeMartino M. P. (ref13/cit13b) 2008; 130 Zhdankin V. V. (ref11/cit11a) 1989; 54 Neilands O. (ref22/cit22a) 1965; 1 Winfield C. J. (ref17/cit17a) 2000 van der Steen F. H. (ref25/cit25a) 1990; 390 Allen A. (ref6/cit6a) 2011; 133 Umemoto T. (ref10/cit10d) 1987; 60 Harvey J. S. (ref6/cit6b) 2011; 133 He Z. (ref18/cit18) 2010; 75 Allen A. E. (ref10/cit10c) 2010; 132 Seebach D. (ref1/cit1a) 1975; 40 Miyata O. (ref1/cit1b) 2013 Chen M. Z. (ref2/cit2b) 2014; 53 Liu C. (ref13/cit13a) 2011; 111 Moriarty R. M. (ref21/cit21) 1981; 22 ref5/cit5b Stauffer S. R. (ref19/cit19) 2000; 43 Rovis T. (ref3/cit3b) 2013; 24 Fernández González D. (ref9/cit9a) 2010; 16 Kieltsch I. (ref10/cit10a) 2007; 46 Skucas E. (ref8/cit8) 2012; 134 Takeda T. (ref20/cit20c) 2013; 135 Zhdankin V. V. (ref5/cit5e) 2008; 108 Adamczyk M. (ref20/cit20a) 1984; 49 Tzirakis M. D. (ref23/cit23) 2013; 113 van der Deen H. (ref24/cit24a) 2000; 2 Koser G. F. (ref15/cit15a) 1982; 47 Moriarty R. M. (ref15/cit15b) 1990 Guo W. (ref26/cit26) 2014; 6 Umemoto T. (ref10/cit10e) 1982; 23 Mastracchio A. (ref12/cit12) 2010; 107 Lee K. (ref2/cit2c) 2012; 51 Eisenberger P. (ref10/cit10b) 2006; 12 Fernández González D. (ref9/cit9b) 2013; 355 Bolm C. (ref25/cit25b) 1995; 1 Mizar P. (ref5/cit5f) 2014; 53 Izquierdo J. (ref2/cit2a) 2012; 51 Malmgren J. (ref27/cit27) 2013; 19 |
| References_xml | – volume: 10 start-page: 4041 year: 2008 ident: WOS:000259197600028 article-title: Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones publication-title: ORGANIC LETTERS doi: 10.1021/ol801574m contributor: fullname: Fernandez-Ibanez, MA – volume: 19 start-page: 10334 year: 2013 ident: WOS:000321983700034 article-title: Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201300860 contributor: fullname: Malmgren, J – start-page: 365 year: 1990 ident: WOS:A1990DN41500001 article-title: [HYDROXY(ORGANOSULFONYLOXY)IODO]ARENES IN ORGANIC-SYNTHESIS publication-title: SYNLETT contributor: fullname: MORIARTY, RM – volume: 111 start-page: 1780 year: 2011 ident: WOS:000288820600015 article-title: Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions publication-title: CHEMICAL REVIEWS doi: 10.1021/cr100379j contributor: fullname: Liu, C – volume: 133 start-page: 4260 year: 2011 ident: WOS:000291715300030 article-title: Enantioselective alpha-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja2008906 contributor: fullname: Allen, AE – volume: 40 start-page: 231 year: 1975 ident: WOS:A1975V343800018 article-title: GENERATION AND SYNTHETIC APPLICATIONS OF 2-LITHIO-1,3-DITHIANES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SEEBACH, D – volume: 22 start-page: 1283 year: 1981 ident: WOS:A1981LG72400001 article-title: DIRECT ALPHA-HYDROXYLATION OF KETONES USING IODOSOBENZENE publication-title: TETRAHEDRON LETTERS contributor: fullname: MORIARTY, RM – volume: 47 start-page: 2487 year: 1982 ident: WOS:A1982NS61000053 article-title: ONE-STEP ALPHA-TOSYLOXYLATION OF KETONES WITH [HYDROXY(TOSYLOXY)IODO]BENZENE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KOSER, GF – volume: 135 start-page: 15306 year: 2013 ident: WOS:000326125200010 article-title: Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged Organosuperbase for the Enantioselective Amination of Ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja408296h contributor: fullname: Takeda, T – volume: 6 start-page: 468 year: 2014 ident: WOS:000337637100010 article-title: Oxidative Breakdown of Iodoalkanes to Catalytically Active Iodine Species: A Case Study in the alpha-Tosyloxylation of Ketones publication-title: CHEMCATCHEM doi: 10.1002/cctc.201300774 contributor: fullname: Guo, WS – volume: 113 start-page: 5262 year: 2013 ident: WOS:000321810600017 article-title: Radical Reactions of Fullerenes: From Synthetic Organic Chemistry to Materials Science and Biology publication-title: CHEMICAL REVIEWS doi: 10.1021/cr300475r contributor: fullname: Tzirakis, MD – volume: 12 start-page: 2579 year: 2006 ident: WOS:000236257800020 article-title: Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200501052 contributor: fullname: Eisenberger, P – volume: 50 start-page: 928 year: 2011 ident: WOS:000287157600025 article-title: Nucleophilic alpha-Arylation and alpha-Alkylation of Ketones by Polarity Inversion of N-Alkoxyenamines: Entry to the Umpolung Reaction at the alpha-Carbon Position of Carbonyl Compounds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201004374 contributor: fullname: Miyoshi, T – volume: 46 start-page: 754 year: 2007 ident: WOS:000243855500019 article-title: Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200603497 contributor: fullname: Kieltsch, I – volume: 1 start-page: 312 year: 1995 ident: WOS:A1995RX52500005 article-title: SYNTHESIS, REACTIONS, AND MOLECULAR-STRUCTURES OF ETHYLZINC ENOLATES OF CHIRAL N-SUBSTITUTED BETA-CARBONYL SULFOXIMINES publication-title: CHEMISTRY-A EUROPEAN JOURNAL contributor: fullname: BOLM, C – volume: 7 start-page: 880 year: 2014 ident: 000348331800029.35 article-title: Oxidative Functionalization with Hypervalent Halides publication-title: Comprehensive Organic Synthesis contributor: fullname: Molander, G. A. – volume: 1 start-page: 1854 year: 1965 ident: 000348331800029.29 publication-title: Zh. Org. Khim. contributor: fullname: Neilands, O. – volume: 53 start-page: 1279 year: 2014 ident: WOS:000336504500012 article-title: Through-Bond/Through-Space Anion Relay Chemistry Exploiting Vinylepoxides as Bifunctional Linchpins publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201309270 contributor: fullname: Chen, MZ – volume: 49 start-page: 4226 year: 1984 ident: WOS:A1984TR09700024 article-title: SYNTHESIS OF BIOLOGICAL MARKERS IN FOSSIL-FUELS .2. SYNTHESIS AND C-13 NMR-STUDIES OF SUBSTITUTED INDANS AND TETRALINS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ADAMCZYK, M – volume: 133 start-page: 13782 year: 2011 ident: WOS:000295241400005 article-title: Enantioselective alpha-Arylation of Carbonyls via Cu(I)-Bisoxazoline Catalysis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja206050b contributor: fullname: Harvey, JS – volume: 390 start-page: C21 year: 1990 ident: WOS:A1990DQ86100015 article-title: SYNTHESIS OF ORGANOZINC ENOLATES OF N,N-DISUBSTITUTED GLYCINE ESTERS - CRYSTAL-STRUCTURE OF [ETZNOC(OME)=C(H)N(TERT-BU)ME]4 publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: VANDERSTEEN, FH – volume: 51 start-page: 11686 year: 2012 ident: WOS:000311702000006 article-title: A Continuum of Progress: Applications of N-Hetereocyclic Carbene Catalysis in Total Synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201203704 contributor: fullname: Izquierdo, J – volume: 43 start-page: 4934 year: 2000 ident: WOS:000166045700004 article-title: Pyrazole ligands: Structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm000170m contributor: fullname: Stauffer, SR – volume: 51 start-page: 5735 year: 2012 ident: WOS:000304814000042 article-title: N-Heterocyclic Carbene Catalyzed Oxidative Macrolactonization: Total Synthesis of (+)-Dactylolide publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201201653 contributor: fullname: Lee, K – volume: 16 start-page: 9457 year: 2010 ident: WOS:000281539500016 article-title: Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201001539 contributor: fullname: Gonzalez, DF – start-page: 60 year: 2013 ident: WOS:000324460900007 article-title: Umpolung reactions at the alpha-carbon position of carbonyl compounds publication-title: ARKIVOC doi: 10.3998/ark.5550190.0014.207 contributor: fullname: Miyata, O – volume: 2002 start-page: 181 year: 2002 ident: WOS:000173118500022 article-title: Investigations on the efficiency of regioselective C-deuteration of endocyclic enolates publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Eames, J – volume: 355 start-page: 1631 year: 2013 ident: WOS:000319420200026 article-title: Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201300266 contributor: fullname: Gonzalez, DF – start-page: 3277 year: 2000 ident: WOS:000089855200014 article-title: Elucidation of the catalytic mechanisms of the non-haem iron-dependent catechol dioxygenases: synthesis of carba-analogues for hydroperoxide reaction intermediates publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 doi: 10.1039/b004265j contributor: fullname: Winfield, CJ – volume: 16 start-page: 8251 year: 2010 ident: WOS:000280819100003 article-title: alpha-Arylation by Rearrangement: On the Reaction of Enolates with Diaryliodonium Salts publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201001110 contributor: fullname: Norrby, PO – year: 2013 ident: 000348331800029.1 – volume: 53 start-page: 5993 year: 2014 ident: WOS:000337094200048 article-title: Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201400405 contributor: fullname: Mizar, P – volume: 101 start-page: 757 year: 2001 ident: WOS:000167639400005 article-title: Catalytic asymmetric organozinc additions to carbonyl compounds publication-title: CHEMICAL REVIEWS doi: 10.1021/cr000411y contributor: fullname: Pu, L – volume: 23 start-page: 1169 year: 1982 ident: WOS:A1982NG71900011 article-title: REACTIONS OF RFI(PH)OSO2CF3 WITH ALKENES AND ALKADIENES publication-title: TETRAHEDRON LETTERS contributor: fullname: UMEMOTO, T – volume: 2 start-page: 488 year: 1966 ident: 000348331800029.30 publication-title: Zh. Org. Khim contributor: fullname: Neilands, O. – volume: 107 start-page: 20648 year: 2010 ident: WOS:000284762400015 article-title: Direct and enantioselective alpha-allylation of ketones via singly occupied molecular orbital (SOMO) catalysis publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA doi: 10.1073/pnas.1002845107 contributor: fullname: Mastracchio, A – volume: 24 start-page: 1188 year: 2013 ident: WOS:000320576300003 article-title: Stable Carbenes: From 'Laboratory Curiosities' to Catalysis Mainstays publication-title: SYNLETT doi: 10.1055/s-0033-1339192 contributor: fullname: Rovis, T – volume: 132 start-page: 4986 year: 2010 ident: WOS:000276553700007 article-title: The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective alpha-Trifluoromethylation of Aldehydes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja100748y contributor: fullname: Allen, AE – volume: 2 start-page: 1593 year: 2000 ident: WOS:000087292600025 article-title: Remarkable O-2-effect in 1,4-additions of diethylzinc to 6-acyloxy-2H-pyran-3(6H)-ones and 6-alkoxy-2H-pyran-3(6H)-ones publication-title: ORGANIC LETTERS contributor: fullname: van der Deen, H – volume: 41 start-page: 3511 year: 2012 ident: WOS:000302559700005 article-title: Organocatalytic umpolung: N-heterocyclic carbenes and beyond publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c2cs15333e contributor: fullname: Bugaut, X – volume: 134 start-page: 9090 year: 2012 ident: WOS:000304837800018 article-title: Enantioselective alpha-Vinylation of Aldehydes via the Synergistic Combination of Copper and Amine Catalysis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja303116v contributor: fullname: Skucas, E – year: 2014 ident: 000348331800029.45 publication-title: Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds contributor: fullname: Zhdankin, V. V. – volume: 60 start-page: 3823 year: 1987 ident: WOS:A1987K702300066 article-title: 1H,1H-PERFLUOROALKYLATION OF ENOL SILYL ETHERS WITH (1H,1H-PERFLUOROALKYL)-PHENYLIODONIUM TRIFLATES - A NEW METHOD FOR THE PREPARATION OF BETA-TRIFLUOROMETHYL AND DELTA-TRIFLUOROMETHYL CARBONYL-COMPOUNDS AND THEIR HIGHER PERFLUOROALKYL HOMOLOGS publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: UMEMOTO, T – volume: 75 start-page: 4636 year: 2010 ident: WOS:000279030900041 article-title: Iodine-Mediated Synthesis of 3H-Indoles via Intramolecular Cyclization of Enamines publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo100796s contributor: fullname: He, ZH – volume: 54 start-page: 2605 year: 1989 ident: WOS:A1989U852000028 article-title: CARBON-CARBON BOND FORMATION IN REACTIONS OF PHIO.HBF4/SILYL ENOL ETHER ADDUCT WITH ALKENES OR SILYL ENOL ETHERS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ZHDANKIN, VV – volume: 108 start-page: 5299 year: 2008 ident: WOS:000261723400011 article-title: Chemistry of Polyvalent Iodine publication-title: CHEMICAL REVIEWS doi: 10.1021/cr800332c contributor: fullname: Zhdankin, VV – volume: 130 start-page: 11546 year: 2008 ident: WOS:000258660600055 article-title: Intermolecular enolate heterocoupling: Scope, mechanism, and application publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja804159y contributor: fullname: DeMartino, MP – volume: 6 start-page: 468 year: 2014 ident: ref26/cit26 publication-title: ChemCatChem doi: 10.1002/cctc.201300774 contributor: fullname: Guo W. – volume: 51 start-page: 5735 year: 2012 ident: ref2/cit2c publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201201653 contributor: fullname: Lee K. – volume: 22 start-page: 1283 year: 1981 ident: ref21/cit21 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)90297-7 contributor: fullname: Moriarty R. M. – volume: 24 start-page: 1188 year: 2013 ident: ref3/cit3b publication-title: Synlett doi: 10.1055/s-0033-1339192 contributor: fullname: Rovis T. – volume: 134 start-page: 9090 year: 2012 ident: ref8/cit8 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja303116v contributor: fullname: Skucas E. – volume: 46 start-page: 754 year: 2007 ident: ref10/cit10a publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200603497 contributor: fullname: Kieltsch I. – start-page: 3277 year: 2000 ident: ref17/cit17a publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/b004265j contributor: fullname: Winfield C. J. – volume: 23 start-page: 1169 year: 1982 ident: ref10/cit10e publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)87051-3 contributor: fullname: Umemoto T. – volume: 41 start-page: 3511 year: 2012 ident: ref3/cit3a publication-title: Chem. Soc. Rev. doi: 10.1039/c2cs15333e contributor: fullname: Bugaut X. – volume: 107 start-page: 20648 year: 2010 ident: ref12/cit12 publication-title: Proc. Natl. Acad. Sci. U.S.A. doi: 10.1073/pnas.1002845107 contributor: fullname: Mastracchio A. – volume: 16 start-page: 8251 year: 2010 ident: ref7/cit7 publication-title: Chem.—Eur. J. doi: 10.1002/chem.201001110 contributor: fullname: Norrby P.-O. – volume: 12 start-page: 2579 year: 2006 ident: ref10/cit10b publication-title: Chem.—Eur. J. doi: 10.1002/chem.200501052 contributor: fullname: Eisenberger P. – volume: 2 start-page: 488 year: 1966 ident: ref22/cit22b publication-title: Zh. Org. Khim contributor: fullname: Neilands O. – volume: 1 start-page: 1854 year: 1965 ident: ref22/cit22a publication-title: Zh. Org. Khim. contributor: fullname: Neilands O. – volume: 19 start-page: 10334 year: 2013 ident: ref27/cit27 publication-title: Chem.—Eur. J. doi: 10.1002/chem.201300860 contributor: fullname: Malmgren J. – start-page: 365 year: 1990 ident: ref15/cit15b publication-title: Synlett doi: 10.1055/s-1990-21097 contributor: fullname: Moriarty R. M. – volume: 75 start-page: 4636 year: 2010 ident: ref18/cit18 publication-title: J. Org. Chem. doi: 10.1021/jo100796s contributor: fullname: He Z. – volume-title: Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds year: 2014 ident: ref5/cit5a contributor: fullname: Zhdankin V. V. – volume: 10 start-page: 4041 year: 2008 ident: ref24/cit24b publication-title: Org. Lett. doi: 10.1021/ol801574m contributor: fullname: Fernández-Ibáňez M. Á. – volume: 355 start-page: 163 year: 2013 ident: ref9/cit9b publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.201300266 contributor: fullname: Fernández González D. – start-page: 60 year: 2013 ident: ref1/cit1b publication-title: ARKIVOC contributor: fullname: Miyata O. – volume: 49 start-page: 4226 year: 1984 ident: ref20/cit20a publication-title: J. Org. Chem. doi: 10.1021/jo00196a024 contributor: fullname: Adamczyk M. – volume: 133 start-page: 13782 year: 2011 ident: ref6/cit6b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja206050b contributor: fullname: Harvey J. S. – volume: 111 start-page: 1780 year: 2011 ident: ref13/cit13a publication-title: Chem. Rev. doi: 10.1021/cr100379j contributor: fullname: Liu C. – volume: 16 start-page: 9457 year: 2010 ident: ref9/cit9a publication-title: Chem.—Eur. J. doi: 10.1002/chem.201001539 contributor: fullname: Fernández González D. – volume: 1 start-page: 212 year: 1995 ident: ref25/cit25b publication-title: Chem.—Eur. J. doi: 10.1002/chem.19950010508 contributor: fullname: Bolm C. – volume: 130 start-page: 11546 year: 2008 ident: ref13/cit13b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja804159y contributor: fullname: DeMartino M. P. – start-page: 181 year: 2002 ident: ref20/cit20b publication-title: Eur. J. Org. Chem. doi: 10.1002/1099-0690(20021)2002:1<181::AID-EJOC181>3.0.CO;2-3 contributor: fullname: Eames J. – volume: 60 start-page: 38 year: 1987 ident: ref10/cit10d publication-title: Bull. Chem. Soc. Jpn. contributor: fullname: Umemoto T. – volume: 135 start-page: 15306 year: 2013 ident: ref20/cit20c publication-title: J. Am. Chem. Soc. doi: 10.1021/ja408296h contributor: fullname: Takeda T. – ident: ref17/cit17b – volume: 53 start-page: 5993 year: 2014 ident: ref5/cit5f publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201400405 contributor: fullname: Mizar P. – volume: 54 start-page: 2605 year: 1989 ident: ref11/cit11a publication-title: J. Org. Chem. doi: 10.1021/jo00272a028 contributor: fullname: Zhdankin V. V. – volume: 113 start-page: 5262 year: 2013 ident: ref23/cit23 publication-title: Chem. Rev. doi: 10.1021/cr300475r contributor: fullname: Tzirakis M. D. – volume: 101 start-page: 757 year: 2001 ident: ref16/cit16 publication-title: Chem. Rev. doi: 10.1021/cr000411y contributor: fullname: Pu L. – volume: 132 start-page: 4986 year: 2010 ident: ref10/cit10c publication-title: J. Am. Chem. Soc. doi: 10.1021/ja100748y contributor: fullname: Allen A. E. – volume: 40 start-page: 231 year: 1975 ident: ref1/cit1a publication-title: J. Org. Chem. doi: 10.1021/jo00890a018 contributor: fullname: Seebach D. – volume: 51 start-page: 11686 year: 2012 ident: ref2/cit2a publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201203704 contributor: fullname: Izquierdo J. – volume: 123 start-page: 958 year: 2011 ident: ref4/cit4 publication-title: Angew. Chem. doi: 10.1002/ange.201004374 contributor: fullname: Miyoshi T. – volume: 390 start-page: C2l year: 1990 ident: ref25/cit25a publication-title: J. Organomet. Chem. doi: 10.1016/0022-328X(90)85039-2 contributor: fullname: van der Steen F. H. – volume: 47 start-page: 2487 year: 1982 ident: ref15/cit15a publication-title: J. Org. Chem. doi: 10.1021/jo00133a053 contributor: fullname: Koser G. F. – volume: 133 start-page: 4260 year: 2011 ident: ref6/cit6a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja2008906 contributor: fullname: Allen A. – volume: 2 start-page: 1593 year: 2000 ident: ref24/cit24a publication-title: Org. Lett. doi: 10.1021/ol005843+ contributor: fullname: van der Deen H. – volume: 43 start-page: 4934 year: 2000 ident: ref19/cit19 publication-title: J. Med. Chem. doi: 10.1021/jm000170m contributor: fullname: Stauffer S. R. – volume: 53 start-page: 1279 year: 2014 ident: ref2/cit2b publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201309270 contributor: fullname: Chen M. Z. – volume: 108 start-page: 5299 year: 2008 ident: ref5/cit5e publication-title: Chem. Rev. doi: 10.1021/cr800332c contributor: fullname: Zhdankin V. V. – ident: ref5/cit5b doi: 10.1016/B978-0-08-097742-3.00735-7 |
| SSID | ssj0011529 |
| Score | 2.3926418 |
| Snippet | We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable... We disclose a hypervalent iodine mediated zeta-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 282 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Oxidative Umpolung α‑Alkylation of Ketones |
| URI | http://dx.doi.org/10.1021/ol503384c http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000348331800029 https://www.ncbi.nlm.nih.gov/pubmed/25562460 https://search.proquest.com/docview/1652382343 |
| Volume | 17 |
| WOS | 000348331800029 |
| WOSCitedRecordID | wos000348331800029 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjZ3JTsMwEIZHpRzgwr6EpQrLNRA7TmIfq0JVgQQHqMQtcmMHoZa2oqkEnHgFHoUX4SF4EsZJUxWVLYdc4lgZz8j_WON8BjikYcC0DDFzo6HABQrOg5IxjQ7RJORCSRZntM-LoNFkZzf-TQkOfqjgU3Lc65hKG2fxDMzS0BXmfIZq7WpcKkABEhkUlXqOQcEU-KDJV430xIOv0jOVT34rPZnM1BfhpPhZJ99d0j4apq2j-Hma3fibBUuwMEoz7WoeF8tQ0t0VmKsVp7utgnP5eKcy6LfdvO9j_HVv7fe3j5fXaqf9lO-Ps3uJfa4NrHuwBs366XWt4YyOTnCkR_zUISTxUXhcr6UC1CiNSWDsKiFkzH2fy7xcSrTru67UQjHpJoEmCeUKP1ThbR3KXex_E2yhcM2VaFxWaIaX12KSa0kMJ0aFjEsLKji20Sj0B1FW1aYkGlttwX4x7FE_R2h812ivcEiEI2GqFrKre0PsL0DPcuoxz4KN3FPjbgw_jbLAteBw0nXj5xl-h3s4b5mZX1hA_tOsNqKjGypAuvWXedswj0mU2QHpkGAHyunDUO9iopK2KlmgfgI5K93v |
| link.rule.ids | 315,783,787,2774,27090,27938,27939,57072,57122 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjZ3JTsMwEEBHUA5wYV_CUgLqNSVOnMQ5VhVV2Q-0Um-RGzsIFVpEUgk48Qt8Cj_CR_AljJ20lEWCHHKJM_J4HM9Y47wBqDiBTyUPMHJzghA3KLgOckolGkSSgIWC01jTPs_9Zpsed7xOgclR_8JgJ1KUlOok_iddgBwMblTCjdF4Gma8wA5UtYJa_XKcMUA_FGo2quNaiggzoghNvqo8UJx-9UA_wspfPZD2No2FvGyR7qc-ZNKrDrNuNX76hnD8nyKLMF8EnWYtnyVLMCX7yzBbH9V6WwHr4uFaaAS42b69w9nYvzLfXt-fX2o3vcf8tJw5SMwTqdDd6Sq0G4etetMqCilY3CVeZhGSeOiGbLcrfPRYEkPC2BZhyGPmeYznyVMibc-2uQwF5XbiS5I4TGBHBd7WoNRH-RtghgJ3YInETYakeLldypnkRFFjREAZN6CMSkfFh5BGOsftkGistQH7o9GP7nKgxm-N9kZ2iXAkVA6D9-VgiPJ8NDBzXOoasJ4bbCxG0dQc6tsGVCYtOH6uYTzMxVVM-YHQAPKfZvWCla4YAdnmX-rtwmyzdXYanR6dn2zBHIZX6mykRfxtKGX3Q7mDIUzWLeu5-wHKKeZY |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3JTsMwEB2xSMCFfQlrQFwDceIkzrEqVGVRQYJKvUVu7CBUaCuSSsCJX-BT-BE-gi9h7KQRm0RzyCXOaCYz9pvROM8A-07gU8kDzNycIMQCBddBTqlEh0gSsFBwGmu2z4Zfb9LTltcqCkX1LwwqkaKkVDfx1azui6RgGCCHvTvVdGM0HodJLyCOOrGgUr0quwaIRaHmR3VcS7HCDJmEvr6qUChOv6PQr9TyTxTSiFObg4tSV73RpHMwyNoH8fMPGsfRjZmH2SL5NCt5tCzAmOwuwnR1eObbElgXj7dCU4Gbzfs-RmX3xnx_-3h5rdx1nvJdc2YvMc-kovBOl6FZO76u1q3iQAWLu8TLLEISD-HIdtvCR-SSmBrGtghDHjPPYzxvohJpe7bNZSgotxNfksRhAhUVeFuBiS7KXwMzFFiJJRKLDUnxctuUM8mJYo8RAWXcgG00PComRBrpXrdDotJqA_aGHoj6ObHGX4N2h76J8EuoXgbvyt4A5fnoZOa41DVgNXdaKUaxqjnUtw3Y_-rF8rkm5WEurmYKD0IDyCjDqgVnuuIKyNb_M28Hpi6PatH5SeNsA2Ywy1JbJC3ib8JE9jCQW5jJZO1tHb6fYB_o0g |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Oxidative+umpolung+%CE%B1-alkylation+of+ketones&rft.jtitle=Organic+letters&rft.au=Shneider%2C+O+Svetlana&rft.au=Pisarevsky%2C+Evgeni&rft.au=Fristrup%2C+Peter&rft.au=Szpilman%2C+Alex+M&rft.date=2015-01-16&rft.eissn=1523-7052&rft.volume=17&rft.issue=2&rft.spage=282&rft_id=info:doi/10.1021%2Fol503384c&rft_id=info%3Apmid%2F25562460&rft.externalDocID=25562460 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon |