Nickel-Catalyzed Ring-Opening Alkylative Coupling of Enone with Methylenecyclopropane in the Presence of Triethylborane
Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C–C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was...
Saved in:
| Published in | Organic letters Vol. 15; no. 6; pp. 1182 - 1185 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
15.03.2013
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C–C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was also accompanied by the β-hydrogen elimination. |
|---|---|
| AbstractList | Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C–C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was also accompanied by the β-hydrogen elimination. Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C-C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was also accompanied by the beta-hydrogen elimination. |
| Author | Shimada, Daisuke Fukuzawa, Shin-ichi Furuya, Shouichi Ogata, Kenichi |
| AuthorAffiliation | Chuo University |
| AuthorAffiliation_xml | – name: Chuo University |
| Author_xml | – sequence: 1 givenname: Kenichi surname: Ogata fullname: Ogata, Kenichi email: kogata@kc.chuo-u.ac.jp, orgsynth@kc.chuo-u.ac.jp – sequence: 2 givenname: Daisuke surname: Shimada fullname: Shimada, Daisuke – sequence: 3 givenname: Shouichi surname: Furuya fullname: Furuya, Shouichi – sequence: 4 givenname: Shin-ichi surname: Fukuzawa fullname: Fukuzawa, Shin-ichi |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23451761$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkU1v1DAQhi1URD_gwB9AuSBRoYAdb2LvsYpaQCoUoXKOHGfMuvXawXZYwq9nwpY9ceA0o5lnRu-8c0qOfPBAyHNG3zBasbfBccrrlfz5iJywuuKloHV1dMgbekxOU7qjlGFl_YQcV3xVM9GwE7L7ZPU9uLJVWbn5FwzFF-u_lTcjeIzFhbufncr2BxRtmEa31IIpLhcBxc7mTfER8mZ24EHP2oUxhlFhy_oib6D4HCGB17DM3Eb7B-1DROIpeWyUS_DsIZ6Rr1eXt-378vrm3Yf24rpUnNW5XFdrGIQRgzGSSUaNWimKtyrQjWoaKXQvzWCoqoSQQJu6HhjwFWile8bkmp-RV_u9qOz7BCl3W5s0OIcawpQ6xpmQXEjRIHq-R3UMKUUw3RjtVsW5Y7RbfO4OPiP74mHt1G9hOJB_jUXg9R7YQR9M0nax4YBRvIE1dUU5ZlQiLf-fbm3GjwSPD_EZR1_uR5VO3V2Yokc7_6H4Nyu5qOM |
| CitedBy_id | crossref_primary_10_1021_acs_chemrev_6b00054 crossref_primary_10_1021_acs_organomet_3c00191 crossref_primary_10_1007_s13738_017_1086_0 crossref_primary_10_1021_acs_chemrev_6b00599 crossref_primary_10_1002_ejoc_201301262 crossref_primary_10_1002_prep_202100230 crossref_primary_10_1021_acscatal_5b00513 crossref_primary_10_1002_adsc_201900327 crossref_primary_10_1002_anie_201405067 crossref_primary_10_1021_jo4019123 crossref_primary_10_1039_C6RA02549H crossref_primary_10_1021_cr400686j crossref_primary_10_1039_C5CC07390A crossref_primary_10_1039_D0OB01211D crossref_primary_10_1002_chin_201329026 crossref_primary_10_1021_jo501423u crossref_primary_10_1002_ange_202303727 crossref_primary_10_1021_acs_orglett_8b03084 crossref_primary_10_1016_j_tet_2014_04_057 crossref_primary_10_1021_acscatal_7b02014 crossref_primary_10_1021_om400876j crossref_primary_10_1039_C5CC01899D crossref_primary_10_1039_D2SC01992B crossref_primary_10_1021_acs_joc_7b03115 crossref_primary_10_1021_jo500948b crossref_primary_10_1002_advs_202400096 crossref_primary_10_1002_ange_201405067 crossref_primary_10_1002_adsc_201601400 crossref_primary_10_1002_anie_202303727 crossref_primary_10_1039_C5DT01516B crossref_primary_10_1039_C3GC41562G crossref_primary_10_1039_D1QO01187A |
| Cites_doi | 10.1021/ja9083607 10.1021/ja072992f 10.1002/anie.201101468 10.1021/ja0608904 10.1021/ja900701g 10.1021/ja049644n 10.1021/ja0660249 10.1021/ol902561r 10.1021/ja0693183 10.1021/ja001440t 10.1021/ol049908a 10.1021/ol801534e 10.1021/ja102262v 10.1021/ja034366y 10.1021/ol101838q 10.1002/anie.200603907 10.1002/anie.200705163 10.1021/ol061579u 10.1021/ja055363j 10.1021/ja903510u 10.1002/chem.201200271 10.1021/ol702543m 10.1246/cl.2012.157 10.1021/ja073300q 10.1002/anie.201004740 10.1021/ja0521831 10.1021/ja9719182 10.1002/cber.19831160103 10.1021/ja803774s 10.1021/ja990997+ 10.1021/ol006781q |
| ContentType | Journal Article |
| Copyright | Copyright © 2013 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2013 American Chemical Society |
| DBID | 1KM 1KN BLEPL DTL GKMDS NPM AAYXX CITATION 7X8 |
| DOI | 10.1021/ol303548x |
| DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2013 PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | Web of Science PubMed CrossRef MEDLINE - Academic |
| DatabaseTitleList | Web of Science MEDLINE - Academic PubMed |
| 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 | 1185 |
| ExternalDocumentID | 10_1021_ol303548x 23451761 000316520300008 a274030378 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: Ministry of Education, Culture, Sports, Science and Technology, Japan; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) |
| 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-929ed7f7dff81810fa4a0035aec6a6687cb8fdf0a2778e0655d1e34ecacb11893 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 32 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000316520300008 |
| ISSN | 1523-7060 |
| IngestDate | Fri Aug 16 01:56:59 EDT 2024 Fri Aug 23 01:50:36 EDT 2024 Tue Aug 27 13:44:54 EDT 2024 Fri Oct 11 20:23:43 EDT 2024 Tue Sep 17 23:21:01 EDT 2024 Thu Aug 27 13:42:10 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 6 |
| Keywords | ALPHA-OLEFINS (+)-ALLOPUMILIOTOXIN 267A ENANTIOSELECTIVE SYNTHESIS ALLYLIC ALCOHOLS SILANES REDUCTIVE COUPLINGS ALDEHYDES ALKYNES SIMPLE ALKENES CONJUGATE ADDITION |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a315t-929ed7f7dff81810fa4a0035aec6a6687cb8fdf0a2778e0655d1e34ecacb11893 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 23451761 |
| PQID | 1317837876 |
| PQPubID | 23479 |
| PageCount | 4 |
| ParticipantIDs | proquest_miscellaneous_1317837876 acs_journals_10_1021_ol303548x pubmed_primary_23451761 webofscience_primary_000316520300008 webofscience_primary_000316520300008CitationCount crossref_primary_10_1021_ol303548x |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
| PublicationCentury | 2000 |
| PublicationDate | 20130315 2013-03-15 2013-Mar-15 |
| PublicationDateYYYYMMDD | 2013-03-15 |
| PublicationDate_xml | – month: 03 year: 2013 text: 20130315 day: 15 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Organic letters |
| PublicationTitleAbbrev | ORG LETT |
| PublicationTitleAlternate | Org. Lett |
| PublicationYear | 2013 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | BINGER, P (WOS:A1983PZ35500002) 1983; 116 Sato, Y (WOS:000251614900067) 2007; 9 Ogata, K (WOS:000292001700021) 2011; 50 Tang, XQ (WOS:000088522700017) 2000; 122 Herath, A (WOS:000241519600030) 2006; 128 McCarren, PR (WOS:000266096900006) 2009; 131 Oblinger, E (WOS:A1997XX82000044) 1997; 119 Chem, K.-M. (000316520300008.4) 1987 Sawaki, R (WOS:000220508600016) 2004; 6 Saito, N (WOS:000258833700045) 2008; 10 Tang, XQ (WOS:000081216800042) 1999; 121 Li, W (WOS:000272185400077) 2009; 131 Sa-ei, K (WOS:000240654700015) 2006; 8 Miller, KM (WOS:000181755800021) 2003; 125 Herath, A (WOS:000247966200021) 2007; 129 Ogata, K (WOS:000282604700027) 2010; 12 Ng, SS (WOS:000232605600037) 2005; 127 Malik, HA (WOS:000272461800042) 2009; 11 Ogata, K (WOS:000303497600005) 2012; 18 Baxer, R. D. (000316520300008.1) 2008; 130 Yang, Y (WOS:000244330800025) 2007; 129 Ng, SS (WOS:000229244600029) 2005; 127 Kimura, M (WOS:000238590000043) 2006; 128 Mahandru, GM (WOS:000220440400014) 2004; 126 Li, W (WOS:000284045400035) 2010; 49 Ogata, K (WOS:000300961000010) 2012; 41 Ho, CY (WOS:000253594300019) 2008; 47 Ho, CY (WOS:000243855500026) 2007; 46 Huang, WS (WOS:000166017300027) 2000; 2 Chaulagain, MR (WOS:000248484400018) 2007; 129 Malik, HA (WOS:000277445400015) 2010; 132 Ogoshi, S (WOS:000268644400008) 2009; 131 Kimura M. (ref3/cit3a) 2006; 128 Ng S.-S. (ref2/cit2a) 2005; 127 Huang W.-S. (ref1/cit1d) 2000; 2 Li W. (ref7/cit7b) 2009; 131 Miller K. M. (ref1/cit1e) 2003; 125 Herath A. (ref7/cit7a) 2007; 129 Baxer R. D. (ref1/cit1j) 2008; 130 Ogata K. (ref6/cit6b) 2012; 18 Yang Y. (ref2/cit2c) 2007; 129 Ho C.-Y. (ref8/cit8a) 2008; 47 Tang X.-Q. (ref1/cit1b) 1999; 121 Ng S.-S. (ref4/cit4) 2005; 127 Ogata K. (ref5/cit5b) 2012; 41 Sato Y. (ref3/cit3c) 2007; 9 Chem K.-M. (ref12/cit12) 1987 Saito N. (ref1/cit1k) 2008; 10 Malik H. A. (ref1/cit1m) 2010; 132 Sa-ei K. (ref1/cit1h) 2006; 8 Tang X.-Q. (ref1/cit1c) 2000; 122 Oblinger E. (ref1/cit1a) 1997; 119 Mahandru G. M. (ref1/cit1f) 2004; 126 Malik H. A. (ref1/cit1l) 2009; 11 Ogoshi S. (ref8/cit8b) 2009; 131 Ogata K. (ref5/cit5a) 2011; 50 Ho C.-Y. (ref2/cit2b) 2007; 46 Chaulagain M. R. (ref1/cit1i) 2007; 129 Li W. (ref7/cit7d) 2010; 49 Binger P. (ref14/cit14) 1983; 116 McCarren P. R. (ref13/cit13) 2009; 131 Herath A. (ref1/cit1g) 2006; 128 Sawaki R. (ref3/cit3b) 2004; 6 Ogata K. (ref6/cit6a) 2010; 12 Herath A. (ref7/cit7c) 2006; 128 |
| References_xml | – volume: 121 start-page: 6098 year: 1999 ident: WOS:000081216800042 article-title: Nickel catalysis in the stereoselective preparation of quinolizidine, pyrrolizidine, and indolizidine alkaloids: Total synthesis of (+)-allopumiliotoxin 267A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Tang, XQ – volume: 131 start-page: 17024 year: 2009 ident: WOS:000272185400077 article-title: Evolution of Efficient Strategies for Enone-Alkyne and Enal-Alkyne Reductive Couplings publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja9083607 contributor: fullname: Li, W – volume: 129 start-page: 9568 year: 2007 ident: WOS:000248484400018 article-title: New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja072992f contributor: fullname: Chaulagain, MR – volume: 50 start-page: 5896 year: 2011 ident: WOS:000292001700021 article-title: Nickel-Catalyzed Three-Component Coupling between Aryl Aldehydes, Norbornenes, and Silanes Leading to Indanols through Aromatic C-H Bond Activation of Aryl Aldehydes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201101468 contributor: fullname: Ogata, K – volume: 128 start-page: 8559 year: 2006 ident: WOS:000238590000043 article-title: Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0608904 contributor: fullname: Kimura, M – volume: 131 start-page: 6654 year: 2009 ident: WOS:000266096900006 article-title: Mechanism and Transition-State Structures for Nickel-Catalyzed Reductive Alkyne-Aldehyde Coupling Reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja900701g contributor: fullname: McCarren, PR – volume: 2 start-page: 4221 year: 2000 ident: WOS:000166017300027 article-title: Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes publication-title: ORGANIC LETTERS contributor: fullname: Huang, WS – volume: 126 start-page: 3698 year: 2004 ident: WOS:000220440400014 article-title: Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja049644n contributor: fullname: Mahandru, GM – volume: 128 start-page: 14030 year: 2006 ident: WOS:000241519600030 article-title: Catalytic intermolecular enal-alkyne [3+2] reductive cycloadditions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0660249 contributor: fullname: Herath, A – volume: 11 start-page: 5734 year: 2009 ident: WOS:000272461800042 article-title: Cooperativity of Regiochemistry Control Strategies in Reductive Couplings of Propargyl Alcohols and Aldehydes publication-title: ORGANIC LETTERS doi: 10.1021/ol902561r contributor: fullname: Malik, HA – volume: 129 start-page: 2248 year: 2007 ident: WOS:000244330800025 article-title: Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: Highly enantioselective synthesis of chiral bishomoallylic alcohols publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0693183 contributor: fullname: Yang, Y – volume: 119 start-page: 9065 year: 1997 ident: WOS:A1997XX82000044 article-title: A new stereoselective method for the preparation of allylic alcohols publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Oblinger, E – volume: 122 start-page: 6950 year: 2000 ident: WOS:000088522700017 article-title: Nickel-catalyzed preparation of bicyclic heterocycles: Total synthesis of (+)-allopumiliotoxin 267A, (+)-allopumiliotoxin 339A, and (+)-allopumiliotoxin 339B publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja001440t contributor: fullname: Tang, XQ – year: 1987 ident: 000316520300008.4 publication-title: J. Chem. Lett. contributor: fullname: Chem, K.-M. – volume: 6 start-page: 1131 year: 2004 ident: WOS:000220508600016 article-title: Ligand-controlled highly stereoselective syntheses of E- and Z-allylsilanes from dienes and aldehydes using nickel complex publication-title: ORGANIC LETTERS doi: 10.1021/ol049908a contributor: fullname: Sawaki, R – volume: 127 start-page: 7320 year: 2005 ident: WOS:000229244600029 article-title: Highly enantioselective and regioselective nickel-catalyzed coupling of allenes, aldehydes, and silanes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Ng, SS – volume: 10 start-page: 3829 year: 2008 ident: WOS:000258833700045 article-title: Nickel-catalyzed highly regioselective multicomponent coupling of ynamides, aldehydes, and silane: A new access to functionalized enamides publication-title: ORGANIC LETTERS doi: 10.1021/ol801534e contributor: fullname: Saito, N – volume: 132 start-page: 6304 year: 2010 ident: WOS:000277445400015 article-title: A General Strategy for Regiocontrol in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja102262v contributor: fullname: Malik, HA – volume: 125 start-page: 3442 year: 2003 ident: WOS:000181755800021 article-title: Catalytic asymmetric reductive coupling of alkynes and aldehydes: Enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034366y contributor: fullname: Miller, KM – volume: 12 start-page: 4536 year: 2010 ident: WOS:000282604700027 article-title: Nickel-Catalyzed Ring-Opening Three-Component Coupling of Methylenecyclopropane with Aldehydes and Silanes publication-title: ORGANIC LETTERS doi: 10.1021/ol101838q contributor: fullname: Ogata, K – volume: 46 start-page: 782 year: 2007 ident: WOS:000243855500026 article-title: Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)(3)}]: Synergy between a strong sigma donor and a strong pi acceptor publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200603907 contributor: fullname: Ho, CY – volume: 47 start-page: 1893 year: 2008 ident: WOS:000253594300019 article-title: alpha-Olefins as alkenylmetal equivalents in catalytic conjugate addition reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200705163 contributor: fullname: Ho, CY – volume: 8 start-page: 4441 year: 2006 ident: WOS:000240654700015 article-title: Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to alpha-silyloxyaldehydes publication-title: ORGANIC LETTERS doi: 10.1021/ol061579u contributor: fullname: Sa-ei, K – volume: 127 start-page: 14194 year: 2005 ident: WOS:000232605600037 article-title: Simple alkenes as substitutes for organometallic reagents: Nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja055363j contributor: fullname: Ng, SS – volume: 131 start-page: 10350 year: 2009 ident: WOS:000268644400008 article-title: Nickel-Catalyzed Direct Conjugate Addition of Simple Alkenes to Enones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja903510u contributor: fullname: Ogoshi, S – volume: 130 start-page: 9662 year: 2008 ident: 000316520300008.1 publication-title: J. Am. Chem. Soc. contributor: fullname: Baxer, R. D. – volume: 18 start-page: 6142 year: 2012 ident: WOS:000303497600005 article-title: Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling between Methylenecyclopropanes, Aldehydes, and Triethylborane with Retention of the Cyclopropane Ring publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201200271 contributor: fullname: Ogata, K – volume: 116 start-page: 1 year: 1983 ident: WOS:A1983PZ35500002 article-title: METALLACYCLOALKANES .6. 5-MEMBERED TO 7-MEMBERED (2,2'-BIPYRIDINE)NICKELACYCLOALKANES FROM METHYLENECYCLOPROPANE AND NICKEL(0) COMPOUNDS publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: BINGER, P – volume: 9 start-page: 5597 year: 2007 ident: WOS:000251614900067 article-title: Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands publication-title: ORGANIC LETTERS doi: 10.1021/ol702543m contributor: fullname: Sato, Y – volume: 41 start-page: 157 year: 2012 ident: WOS:000300961000010 article-title: Nickel-catalyzed Diastereoselective Reductive Coupling Reaction of Norbornene with Aldehydes in the Presence of Triethylborane publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2012.157 contributor: fullname: Ogata, K – volume: 129 start-page: 8712 year: 2007 ident: WOS:000247966200021 article-title: Catalytic intermolecular reductive coupling of enones and alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja073300q contributor: fullname: Herath, A – volume: 49 start-page: 8712 year: 2010 ident: WOS:000284045400035 article-title: Regioselective Nickel-Catalyzed Reductive Couplings of Enones and Allenes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201004740 contributor: fullname: Li, W – volume: 129 start-page: 8712 year: 2007 ident: ref7/cit7a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja073300q contributor: fullname: Herath A. – volume: 127 start-page: 14194 year: 2005 ident: ref2/cit2a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja055363j contributor: fullname: Ng S.-S. – volume: 125 start-page: 3442 year: 2003 ident: ref1/cit1e publication-title: J. Am. Chem. Soc. doi: 10.1021/ja034366y contributor: fullname: Miller K. M. – volume: 46 start-page: 782 year: 2007 ident: ref2/cit2b publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200603907 contributor: fullname: Ho C.-Y. – volume: 127 start-page: 7320 year: 2005 ident: ref4/cit4 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0521831 contributor: fullname: Ng S.-S. – volume: 41 start-page: 157 year: 2012 ident: ref5/cit5b publication-title: Chem. Lett. doi: 10.1246/cl.2012.157 contributor: fullname: Ogata K. – volume: 128 start-page: 14030 year: 2006 ident: ref7/cit7c publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0660249 contributor: fullname: Herath A. – volume: 49 start-page: 8712 year: 2010 ident: ref7/cit7d publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201004740 contributor: fullname: Li W. – volume: 6 start-page: 1131 year: 2004 ident: ref3/cit3b publication-title: Org. Lett. doi: 10.1021/ol049908a contributor: fullname: Sawaki R. – volume: 10 start-page: 3829 year: 2008 ident: ref1/cit1k publication-title: Org. Lett. doi: 10.1021/ol801534e contributor: fullname: Saito N. – volume: 11 start-page: 5734 year: 2009 ident: ref1/cit1l publication-title: Org. Lett. doi: 10.1021/ol902561r contributor: fullname: Malik H. A. – volume: 131 start-page: 17024 year: 2009 ident: ref7/cit7b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja9083607 contributor: fullname: Li W. – volume: 126 start-page: 3698 year: 2004 ident: ref1/cit1f publication-title: J. Am. Chem. Soc. doi: 10.1021/ja049644n contributor: fullname: Mahandru G. M. – volume: 119 start-page: 9065 year: 1997 ident: ref1/cit1a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja9719182 contributor: fullname: Oblinger E. – volume: 116 start-page: 1 year: 1983 ident: ref14/cit14 publication-title: Chem. Ber. doi: 10.1002/cber.19831160103 contributor: fullname: Binger P. – volume: 129 start-page: 2248 year: 2007 ident: ref2/cit2c publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0693183 contributor: fullname: Yang Y. – volume: 122 start-page: 6950 year: 2000 ident: ref1/cit1c publication-title: J. Am. Chem. Soc. doi: 10.1021/ja001440t contributor: fullname: Tang X.-Q. – start-page: 1923 year: 1987 ident: ref12/cit12 publication-title: Chem. Lett. contributor: fullname: Chem K.-M. – volume: 128 start-page: 14030 year: 2006 ident: ref1/cit1g publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0660249 contributor: fullname: Herath A. – volume: 128 start-page: 8559 year: 2006 ident: ref3/cit3a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0608904 contributor: fullname: Kimura M. – volume: 12 start-page: 4536 year: 2010 ident: ref6/cit6a publication-title: Org. Lett. doi: 10.1021/ol101838q contributor: fullname: Ogata K. – volume: 50 start-page: 5896 year: 2011 ident: ref5/cit5a publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201101468 contributor: fullname: Ogata K. – volume: 47 start-page: 1893 year: 2008 ident: ref8/cit8a publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200705163 contributor: fullname: Ho C.-Y. – volume: 132 start-page: 6304 year: 2010 ident: ref1/cit1m publication-title: J. Am. Chem. Soc. doi: 10.1021/ja102262v contributor: fullname: Malik H. A. – volume: 8 start-page: 4441 year: 2006 ident: ref1/cit1h publication-title: Org. Lett. doi: 10.1021/ol061579u contributor: fullname: Sa-ei K. – volume: 131 start-page: 10350 year: 2009 ident: ref8/cit8b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja903510u contributor: fullname: Ogoshi S. – volume: 130 start-page: 9662 year: 2008 ident: ref1/cit1j publication-title: J. Am. Chem. Soc. doi: 10.1021/ja803774s contributor: fullname: Baxer R. D. – volume: 9 start-page: 5597 year: 2007 ident: ref3/cit3c publication-title: Org. Lett. doi: 10.1021/ol702543m contributor: fullname: Sato Y. – volume: 121 start-page: 6098 year: 1999 ident: ref1/cit1b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja990997+ contributor: fullname: Tang X.-Q. – volume: 129 start-page: 9568 year: 2007 ident: ref1/cit1i publication-title: J. Am. Chem. Soc. doi: 10.1021/ja072992f contributor: fullname: Chaulagain M. R. – volume: 131 start-page: 6654 year: 2009 ident: ref13/cit13 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja900701g contributor: fullname: McCarren P. R. – volume: 2 start-page: 4221 year: 2000 ident: ref1/cit1d publication-title: Org. Lett. doi: 10.1021/ol006781q contributor: fullname: Huang W.-S. – volume: 18 start-page: 6142 year: 2012 ident: ref6/cit6b publication-title: Chem.—Eur. J. doi: 10.1002/chem.201200271 contributor: fullname: Ogata K. |
| SSID | ssj0011529 |
| Score | 2.2955096 |
| Snippet | Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 1182 |
| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Nickel-Catalyzed Ring-Opening Alkylative Coupling of Enone with Methylenecyclopropane in the Presence of Triethylborane |
| URI | http://dx.doi.org/10.1021/ol303548x http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000316520300008 https://www.ncbi.nlm.nih.gov/pubmed/23451761 https://search.proquest.com/docview/1317837876 |
| Volume | 15 |
| WOS | 000316520300008 |
| WOSCitedRecordID | wos000316520300008 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1NT9wwEB0hemgvhX6nFOS2XE1xYsfr4yqAUCWqqgWJWxQ746raKKlKVmj59Z3JblZU0I9TDrEt2zP2e_bYzwD7mYs0agxKb2rNWzdeOqNROh9Raes1Dqfdzz7lpxf646W53ID3f4jgp-pD19AsS7yaiOKDlPCQV1jT4us6VEAA5AZR1DSTLAUzygfdzsrQE65-h547fPJe6Blg5mQLjsbLOsvTJbODee8Pws1d7ca_tWAbHq9oppgu_eIJbGD7FB4W4-tuz-CaXGCGjSx4-2Zxg7X4QiAm-XwJfcW0mS2aQRNcFN2cb-1-E10Ux23XouC9W3GGZGKCLAyL0HRUX5pWUHxvBTFK8Xm41BSQ85zTYpyTsrO1-BwuTo7Pi1O5eoRBVpkyvST6hLWNto6RsF0dxkpXHH6sMORVnk9s8JNYx8MqtXaCRGhMrTDTGKrgafHishewyXV7BcJUJnPochMpgUftfDA-qpo5Q-q0TWCPrFSuBtFVOcTHU1Wu-y-Bd6MByx9LMY77Er0dTVtSn3L8g1rXzak84kqsn2_zBF4ubb4uJs20UTZXCezfdoL1f147qtykNCcybUpA_U-yYqWzzvoC_et_NW8HHqXDYxuZVOYNbPY_57hLlKf3e4PL_wIdyft_ |
| link.rule.ids | 315,786,790,2782,27107,27955,27956,57091,57141 |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Nb9QwELVQOZQL39BQKAb16lIndrw-VlGrBboVgq3UWxQ7Y4Q2Sio2K7T99Z3xZpcClegph9iWP8Z-zx77DWP7mQ04azQIp2tFRzdOWK1AWBdAKuMUxNvuk7N8fK4-XeiLQSaH3sJgJeZY0jw68X-rC8gPXYOLLdJr5Iv3tUGUIxpUfNt4DBCHbNRGTTNBijBrFaGbWQmB_PxPBPqHVt6KQBFtTh6twhbFesZLJrODRe8O_NVfEo53a8hj9nAgnfxoZSVP2D1on7LtYh3r7Rn7hQYxg0YUdJizvIKaf0VIE3TbBL_8qJktm6gQzotuQW94v_Mu8OO2a4HTSS6fAA44Ahj4pW86rDYuMsB_tBz5Jf8Snzh5oDxT3JpTUjK9Fp6z85PjaTEWQ0gGUWVS9wLJFNQmmDoERHp5GCpVkTOyAp9XeT4y3o1CHQ6r1JgRIL3RtYRMga-8w62MzV6wLarbDuO60pkFm-uACRwo67x2QdbEIFKrTML2sPvKYUrNy-gtT2W56b-EvV-PY3m5kua4LdG79QiX2KfkDcHWdQssD5kTqembPGEvV0O_KSbNlJYmlwnbv2kLm_-0k5S5TnGFJBKVMHmXZMWguk5qA_2r_zXvLdseTyen5enHs8-77EEaw3BkQurXbKv_uYA3SIZ6txdnwTXAkAP5 |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwELZQkYAL70d4FIN6dakTO14fV6Gr8mipoJV6i2JnjNBGScVmhba_nhlvNipQiZ5yiG2N7RnPNx77M2M7mQ1oNRqE07WirRsnrFYgrAsglXEK4mn3w6P84FR9PNNnQ6BId2FQiAW2tIhJfLLq8zoMDAPyXdfggosQGzHjTW2kIkOcFt_GrAH6Ihv5UdNMECvMhknoclXyQn7xpxf6B1pe6YWix5ndY19GWeNBk_nusne7_uIvGsfrd-Y-uzuATz5da8sDdgPah-x2sXnz7RH7hYoxh0YUtKmzuoCaf0XXJujUCX75tJmvmsgUzotuSXd5v_Mu8P22a4HTji4_BJx4dGTgV77pUHRcbID_aDniTH4crzp5oDonGKJTUVLBFh6z09n-SXEghqcZRJVJ3QsEVVCbYOoQ0OPLvVCpipKSFfi8yvOJ8W4S6rBXpcZMAGGOriVkCnzlHYY0NnvCtki2Z4zrSmcWbK4DFnCgrPPaBVkTkkitMgnbxiEsB9NalDFrnspyHL-Evd3MZXm-pui4qtCbzSyXOKaUFcHedUtsDxEUseqbPGFP19M_NpNmSkuTy4TtXNaH8T9FlDLXKa6UBKYSJq9TrBjY14l1oH_-v-69ZreO38_Kzx-OPr1gd9L4GkcmpH7JtvqfS3iFmKh329EQfgMVKgZz |
| 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=Nickel-Catalyzed+Ring-Opening+Alkylative+Coupling+of+Enone+with+Methylenecyclopropane+in+the+Presence+of+Triethylborane&rft.jtitle=Organic+letters&rft.au=Ogata%2C+Kenichi&rft.au=Shimada%2C+Daisuke&rft.au=Furuya%2C+Shouichi&rft.au=Fukuzawa%2C+Shin-ichi&rft.date=2013-03-15&rft.pub=American+Chemical+Society&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=15&rft.issue=6&rft.spage=1182&rft.epage=1185&rft_id=info:doi/10.1021%2Fol303548x&rft.externalDocID=a274030378 |
| 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 |