Facile, Novel Methodology for the Synthesis of Spiro[pyrrolidin-3,3′-oxindoles]: Catalyzed Ring Expansion Reactions of Cyclopropanes by Aldimines
The role of the bifunctional catalyst is decisive: The magnesium ion as Lewis acid and its nucleophilic iodide counterion contribute in synergy to the successful ring expansion of the cyclopropane 1 by aldimine 2 [Eq. (1)]. This reaction offers a novel route to spiro[pyrrolidin‐3,3′‐oxindoles] 3....
Saved in:
| Published in | Angewandte Chemie (International ed.) Vol. 38; no. 21; pp. 3186 - 3189 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag GmbH
02.11.1999
WILEY‐VCH Verlag GmbH Wiley |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | The role of the bifunctional catalyst is decisive: The magnesium ion as Lewis acid and its nucleophilic iodide counterion contribute in synergy to the successful ring expansion of the cyclopropane 1 by aldimine 2 [Eq. (1)]. This reaction offers a novel route to spiro[pyrrolidin‐3,3′‐oxindoles] 3. |
|---|---|
| AbstractList | The role of the bifunctional catalyst is decisive: The magnesium ion as Lewis acid and its nucleophilic iodide counterion contribute in synergy to the successful ring expansion of the cyclopropane 1 by aldimine 2 [Eq. (1)]. This reaction offers a novel route to spiro[pyrrolidin‐3,3′‐oxindoles] 3. |
| Author | Alper, Phil B. Siegel, Dionicio R. Carreira, Erick M. Meyers, Christiane Lerchner, Andreas |
| Author_xml | – sequence: 1 givenname: Phil B. surname: Alper fullname: Alper, Phil B. organization: Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich, Switzerland, Fax: (+41) 1-632-13-28 – sequence: 2 givenname: Christiane surname: Meyers fullname: Meyers, Christiane organization: Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich, Switzerland, Fax: (+41) 1-632-13-28 – sequence: 3 givenname: Andreas surname: Lerchner fullname: Lerchner, Andreas organization: Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich, Switzerland, Fax: (+41) 1-632-13-28 – sequence: 4 givenname: Dionicio R. surname: Siegel fullname: Siegel, Dionicio R. organization: Arnold and Mabel Beckman Laboratory for Chemical Synthesis, California Institute of Technology, Pasadena, CA 91125, USA – sequence: 5 givenname: Erick M. surname: Carreira fullname: Carreira, Erick M. email: carreira@org.chem.ethz.ch organization: Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich, Switzerland, Fax: (+41) 1-632-13-28 |
| BookMark | eNqNUd1u0zAUjtAQ-4F38GUnlmLHdeyUCalk3VZttNIK4gLQwU6czZDGJU6h4Yp34E14JJ4Eh269QUjzzfnx-b7z8-0HO5WtdBCcENwnGEfPevNJOjkkLCIh5Zz2SJIkhODokIphRI4pEfFwOJqchKPpZNxFL2gf99PZ8ygcPwj2tsAd7w8oDblgZDfYd-6TZxcCx4-CXYIZi0XC94KfpzIzpT5CU_tVl-iVbm5sbkt73aLC1qi50WjeVt4445At0Hxpavtu2da1LU1uqpAe0d8_foV2bSqP0-7DEKWykWX7XefoylTXaLxeysoZW6ErLbPGO3-Z0jYr7bK2_lM7pFo0KnOzMD54HDwsZOn0k1t7ELw5Hb9Oz8PL2dkkHV2G2SAexKEq4kRiWRQsk5lKFOUsj5UWMVVKJSJSXBDC_KIEa6wHnKuiICrBEWYyifOcHgS9Da-f4stKuwYWxmW6LP1EduWAcNwdHieRL32_Kc1q61ytC1jWZiHrFgiGTjaATjborg_d9eFONqACupwXCsDLBneyAQUM6QwiGHt6saH_ppUtXGZ0leltC-yfoIwJ7h3CUtPI7oqpXVWNhz69P9RXf7yt9qK3_yxxjx3-s8I251uEmxbGNXq9bSHrzxBzrxG8nZ5BdMH5xflLDoL-AaL04DM |
| ContentType | Journal Article |
| Copyright | Copyright © 1999 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany |
| Copyright_xml | – notice: Copyright © 1999 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany |
| DBID | BSCLL 1KM 1KN BLEPL DTL FGRAT AAYXX CITATION 7SR 8BQ 8FD JG9 |
| DOI | 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO;2-E |
| DatabaseName | Istex Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 1999 CrossRef Engineered Materials Abstracts METADEX Technology Research Database Materials Research Database |
| DatabaseTitle | Web of Science CrossRef Materials Research Database Engineered Materials Abstracts Technology Research Database METADEX |
| DatabaseTitleList | Materials Research Database |
| Database_xml | – sequence: 1 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 | 1521-3773 |
| EndPage | 3189 |
| ExternalDocumentID | 10_1002__SICI_1521_3773_19991102_38_21_3186__AID_ANIE3186_3_0_CO_2_E 000083558700015 ANIE3186 ark_67375_WNG_2K77KHB7_8 |
| Genre | shortCommunication |
| GroupedDBID | --- -DZ -~X .3N .GA .GJ .Y3 05W 0R~ 0ZS 10A 186 1L6 1OB 1OC 1ZS 23M 31~ 33P 3SF 3WU 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5RE 5VS 66C 6TJ 702 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 9M8 A03 AAESR AAEVG AAHHS AANLZ AAONW AASGY AAXRX AAZKR ABCQN ABCUV ABEFU ABEML ABHUG ABIJN ABLJU ABPPZ ABPVW ABTAH ABWRO ACAHQ ACBWZ ACCFJ ACCZN ACFBH ACGFS ACIWK ACNCT ACPOU ACPRK ACSCC ACSMX ACXBN ACXME ACXQS ADAWD ADBBV ADDAD ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AEQDE AETEA AEUQT AEUYR AFBPY AFDAS AFFNX AFFPM AFGKR AFMIJ AFPWT AFRAH AFVGU AFZJQ AGJLS AHBTC AHMBA AI. AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ATUGU AUFTA AZBYB AZFZN AZVAB B-7 BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BSCLL BTSUX BY8 CS3 D-E D-F D0L DCZOG DPXWK DR1 DR2 DRFUL DRSTM EBS EJD F00 F01 F04 F5P FEDTE G-S G.N G8K GNP GODZA H.T H.X HBH HHY HHZ HVGLF HZ~ H~9 IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MVM MXFUL MXSTM N04 N05 N9A NF~ NHB NNB O66 O9- P2P P2W P2X P4D PQQKQ Q.N Q11 QB0 QRW R.K RNS ROL RWI RX1 S10 SUPJJ TN5 UB1 UPT V2E VH1 VQA W8V W99 WBFHL WBKPD WH7 WIB WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XFK XG1 XPP XSW XV2 YZZ ZCG ZGI ZXP ZY4 ZZTAW ~IA ~KM ~WT AITYG HGLYW M53 OIG 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED AAYXX CITATION 7SR 8BQ 8FD JG9 |
| ID | FETCH-LOGICAL-c4646-bf69a0aff5cacb9b375d6be863bbb982b7811555610e0e477bff1b90205a96dd3 |
| IEDL.DBID | DR2 |
| ISICitedReferencesCount | 265 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000083558700015 |
| ISSN | 1433-7851 |
| IngestDate | Fri Aug 16 00:33:17 EDT 2024 Thu Sep 26 17:14:17 EDT 2024 Fri Sep 27 16:38:35 EDT 2024 Wed Sep 18 01:59:13 EDT 2024 Sat Aug 24 00:44:41 EDT 2024 Wed Jan 17 05:00:25 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 21 |
| Keywords | ORGANIC-SYNTHESIS ASYMMETRIC-SYNTHESIS STEREOCONTROLLED TOTAL SYNTHESIS ring expansions alkaloids cyclopropanes nucleophilic additions spiro compounds DERIVATIVES (+/-)-GELSEMINE EFFICIENT |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c4646-bf69a0aff5cacb9b375d6be863bbb982b7811555610e0e477bff1b90205a96dd3 |
| Notes | ark:/67375/WNG-2K77KHB7-8 ArticleID:ANIE3186 istex:272C3DC9553EC888D5488AD3B43C2BE0A451F638 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0003-1472-490X |
| PMID | 10556897 |
| PQID | 1701102092 |
| PQPubID | 23500 |
| PageCount | 4 |
| ParticipantIDs | proquest_miscellaneous_1701102092 crossref_primary_10_1002__SICI_1521_3773_19991102_38_21_3186__AID_ANIE3186_3_0_CO_2_E webofscience_primary_000083558700015 webofscience_primary_000083558700015CitationCount istex_primary_ark_67375_WNG_2K77KHB7_8 wiley_primary_10_1002_SICI_1521_3773_19991102_38_21_3186_AID_ANIE3186_3_0_CO_2_E_ANIE3186 |
| PublicationCentury | 1900 |
| PublicationDate | November 2, 1999 |
| PublicationDateYYYYMMDD | 1999-11-02 |
| PublicationDate_xml | – month: 11 year: 1999 text: November 2, 1999 day: 02 |
| PublicationDecade | 1990 |
| PublicationPlace | Weinheim |
| PublicationPlace_xml | – name: Weinheim – name: BERLIN |
| PublicationTitle | Angewandte Chemie (International ed.) |
| PublicationTitleAbbrev | ANGEW CHEM INT EDIT |
| PublicationTitleAlternate | Angew. Chem. Int. Ed |
| PublicationYear | 1999 |
| Publisher | WILEY-VCH Verlag GmbH WILEY‐VCH Verlag GmbH Wiley |
| Publisher_xml | – name: WILEY-VCH Verlag GmbH – name: WILEY‐VCH Verlag GmbH – name: Wiley |
| References | Kuehne, ME (WOS:000077498400047) 1998; 63 COX, ED (WOS:A1995RY99500005) 1995; 95 WONG, HNC (WOS:A1989T169000005) 1989; 89 CRESTINI, C (WOS:A1994PM82900002) 1994; 24 Gan, T (WOS:000071410200058) 1997; 62 Mish, MR (WOS:A1997XU61400034) 1997; 119 Corey, EJ (WOS:000072624500014) 1998; 120 LECLERCQ, J (WOS:A1986C303400008) 1986; 15 Fukuyama, T (WOS:A1996VB31000034) 1996; 118 BAGNELL, L (WOS:A1975AB55300017) 1975; 28 Edmondson, S (WOS:000079242800018) 1999; 121 Tomooka, CS (WOS:000083701300039) 1999; 1 DUPONT PL (WOS:000083558700015.15) 1977; 33 KUTNEY JP (WOS:000083558700015.26) 1977; 3 Whitlock, GA (WOS:A1997YG45200009) 1997; 62 ALBRECHT, R (WOS:A19648534A00001) 1964; 97 DuBois, J (WOS:A1996TT38100033) 1996; 118 DuBois, J (WOS:A1997WR15000034) 1997; 119 DuBois, J (WOS:A1997XW34200003) 1997; 30 He, F (WOS:000081603000037) 1999; 121 CORDELL GA (WOS:000083558700015.6) 1998; 5 Atarashi, S (WOS:A1997XJ83300003) 1997; 119 Edmondson, SD (WOS:000073570300028) 1998; 37 Ashimori, A (WOS:000074727600007) 1998; 120 Matsuura, T (WOS:000074727600009) 1998; 120 EVANS, DA (WOS:A1974S944500004) 1974; 7 Kozmin, SA (WOS:000077874300035) 1998; 120 Cushing, TD (WOS:A1996TR63300008) 1996; 118 DANISHEFSKY, S (WOS:A1979GH92900004) 1979; 12 Kuehne, ME (WOS:A1996VE27200053) 1996; 61 CLAXGON GP (WOS:000083558700015.5) 1988; 6 SMITH, AB (WOS:A1978EX31300012) 1978 Saxton, JE (WOS:A1997YK19600002) 1997; 14 EDMONDSON SD (WOS:000083558700015.16) 1998; 110 |
| References_xml | – volume: 110 start-page: 1190 year: 1998 ident: WOS:000083558700015.16 publication-title: ANGEW CHEM contributor: fullname: EDMONDSON SD – volume: 118 start-page: 915 year: 1996 ident: WOS:A1996TT38100033 article-title: Nitrogen transfer from a nitridomanganese(V) complex: Amination of silyl enol ethers publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: DuBois, J – volume: 37 start-page: 1138 year: 1998 ident: WOS:000073570300028 article-title: The total synthesis of spirotryprostatin A publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Edmondson, SD – volume: 121 start-page: 6771 year: 1999 ident: WOS:000081603000037 article-title: Enantioselective total synthesis of aspidophytine publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: He, F – volume: 3 start-page: 273 year: 1977 ident: WOS:000083558700015.26 publication-title: TOTAL SYNTHESIS NATU contributor: fullname: KUTNEY JP – volume: 63 start-page: 9434 year: 1998 ident: WOS:000077498400047 article-title: Syntheses of strychnan- and aspidospermatan-type alkaloids. 11. Total syntheses of (-)-lochneridine and (-)- and racemic 20-epi-lochneridine publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kuehne, ME – volume: 121 start-page: 2147 year: 1999 ident: WOS:000079242800018 article-title: Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Edmondson, S – volume: 6 start-page: 968 year: 1988 ident: WOS:000083558700015.5 publication-title: ORG SYNTH COLL contributor: fullname: CLAXGON GP – volume: 119 start-page: 8379 year: 1997 ident: WOS:A1997XU61400034 article-title: Asymmetric dipolar cycloadditions of Me3SiCHN2. Synthesis of a novel class of amino acids: Azaprolines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Mish, MR – volume: 5 year: 1998 ident: WOS:000083558700015.6 publication-title: ALKALOIDS CHEM BIOL contributor: fullname: CORDELL GA – volume: 30 start-page: 364 year: 1997 ident: WOS:A1997XW34200003 article-title: Nitridomanganese(V) complexes: Design, preparation, and use as nitrogen atom-transfer reagents publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: DuBois, J – volume: 28 start-page: 821 year: 1975 ident: WOS:A1975AB55300017 article-title: ORGANOALUMINUM COMPOUNDS .31. NICKEL-CATALYZED CONJUGATE ADDITION OF TRIMETHYLALUMINUM TO CYCLOPROPYL KETONES publication-title: AUSTRALIAN JOURNAL OF CHEMISTRY contributor: fullname: BAGNELL, L – volume: 118 start-page: 7426 year: 1996 ident: WOS:A1996VB31000034 article-title: Stereocontrolled total synthesis of (+/-)-gelsemine publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Fukuyama, T – volume: 61 start-page: 6001 year: 1996 ident: WOS:A1996VE27200053 article-title: Total syntheses of vincadifformine, 3-oxovincadifformine, pseudo- and 20-epi-pseudovincadifformine, tabersonine, and Delta(18)-tabersonine through radical reactions and Heck reaction publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kuehne, ME – volume: 24 start-page: 2835 year: 1994 ident: WOS:A1994PM82900002 article-title: A NEW EFFICIENT AND MILD SYNTHESIS OF 2-OXINDOLES BY ONE-POT WOLFF-KISHNER LIKE REDUCTION OF ISATIN DERIVATIVES publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: CRESTINI, C – volume: 62 start-page: 7916 year: 1997 ident: WOS:A1997YG45200009 article-title: Enantioselective synthesis of ent-stellettamide A via a novel dipolar cycloaddition reaction of (Trimethylsilyl)diazomethane publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Whitlock, GA – volume: 120 start-page: 6477 year: 1998 ident: WOS:000074727600007 article-title: Catalytic asymmetric synthesis of quaternary carbon centers. Exploratory investigations of intramolecular Heck reactions of (E)-alpha,beta-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Ashimori, A – volume: 14 start-page: 559 year: 1997 ident: WOS:A1997YK19600002 article-title: Recent progress in the chemistry of the monoterpenoid indole alkaloids publication-title: NATURAL PRODUCT REPORTS contributor: fullname: Saxton, JE – volume: 120 start-page: 2330 year: 1998 ident: WOS:000072624500014 article-title: A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Corey, EJ – volume: 1 start-page: 149 year: 1999 ident: WOS:000083701300039 article-title: N,O-bis(trifluoroacetyl)hydroxylamine as a useful electrophilic nitrogen source: Catalytic synthesis of N-(trifluoroacetyl)sulfilimines publication-title: ORGANIC LETTERS contributor: fullname: Tomooka, CS – volume: 62 start-page: 9298 year: 1997 ident: WOS:000071410200058 article-title: Enantiospecific synthesis of optically active 6-methoxytryptophan derivatives and total synthesis of tryprostatin A publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Gan, T – volume: 89 start-page: 165 year: 1989 ident: WOS:A1989T169000005 article-title: USE OF CYCLOPROPANES AND THEIR DERIVATIVES IN ORGANIC-SYNTHESIS publication-title: CHEMICAL REVIEWS contributor: fullname: WONG, HNC – volume: 12 start-page: 66 year: 1979 ident: WOS:A1979GH92900004 article-title: ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: DANISHEFSKY, S – volume: 7 start-page: 147 year: 1974 ident: WOS:A1974S944500004 article-title: ALLYLIC SULFOXIDES - USEFUL INTERMEDIATES IN ORGANIC SYNTHESIS publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: EVANS, DA – volume: 118 start-page: 557 year: 1996 ident: WOS:A1996TR63300008 article-title: Stereocontrolled total synthesis of (+)-paraherquamide B publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Cushing, TD – volume: 15 start-page: 305 year: 1986 ident: WOS:A1986C303400008 article-title: SCREENING OF CYTOTOXIC ACTIVITIES OF STRYCHNOS ALKALOIDS (METHODS AND RESULTS) publication-title: JOURNAL OF ETHNOPHARMACOLOGY contributor: fullname: LECLERCQ, J – volume: 120 start-page: 6500 year: 1998 ident: WOS:000074727600009 article-title: Catalytic asymmetric synthesis of either enantiomer of the Calabar alkaloids physostigmine and physovenine publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Matsuura, T – volume: 33 start-page: 1801 year: 1977 ident: WOS:000083558700015.15 publication-title: ACTA CRYSTALLOGR B contributor: fullname: DUPONT PL – volume: 119 start-page: 6226 year: 1997 ident: WOS:A1997XJ83300003 article-title: Free radical cyclizations in alkaloid total synthesis: (+/-)-21-oxogelsemine and (+/-)-gelsemine publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Atarashi, S – start-page: 1649 year: 1978 ident: WOS:A1978EX31300012 article-title: NUCLEOPHILIC RING CLEAVAGE OF MONO-ACTIVATED CYCLOPROPANES VIA SODIUM AND LITHIUM PHENYL SELENOLATE publication-title: TETRAHEDRON LETTERS contributor: fullname: SMITH, AB – volume: 119 start-page: 3179 year: 1997 ident: WOS:A1997WR15000034 article-title: Novel, stereoselective synthesis of 2-amino saccharides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: DuBois, J – volume: 97 start-page: 483 year: 1964 ident: WOS:A19648534A00001 article-title: ARYLSULFONYLIMINE - DARSTELLUNG EIGENSCHAFTEN UND REAKTIVITAT publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: ALBRECHT, R – volume: 120 start-page: 13523 year: 1998 ident: WOS:000077874300035 article-title: A general strategy to Aspidosperma alkaloids: Efficient, stereocontrolled synthesis of tabersonine publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Kozmin, SA – volume: 95 start-page: 1797 year: 1995 ident: WOS:A1995RY99500005 article-title: THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION publication-title: CHEMICAL REVIEWS contributor: fullname: COX, ED |
| SSID | ssj0028806 |
| Score | 2.169107 |
| Snippet | The role of the bifunctional catalyst is decisive: The magnesium ion as Lewis acid and its nucleophilic iodide counterion contribute in synergy to the... |
| Source | Web of Science |
| SourceID | proquest crossref webofscience wiley istex |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 3186 |
| SubjectTerms | Alkaloids Catalysts Chemistry Chemistry, Multidisciplinary Cyclopropanes Iodides Lewis acid Magnesium Methodology Nucleophilic additions Organic compounds Physical Sciences Ring expansions Science & Technology Spiro compounds Synthesis |
| Title | Facile, Novel Methodology for the Synthesis of Spiro[pyrrolidin-3,3′-oxindoles]: Catalyzed Ring Expansion Reactions of Cyclopropanes by Aldimines |
| URI | https://api.istex.fr/ark:/67375/WNG-2K77KHB7-8/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2F%28SICI%291521-3773%2819991102%2938%3A21%3C3186%3A%3AAID-ANIE3186%3E3.0.CO%3B2-E http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000083558700015 https://search.proquest.com/docview/1701102092 |
| Volume | 38 |
| WOS | 000083558700015 |
| WOSCitedRecordID | wos000083558700015 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwxV3datswFBalg203-x_z_tCgHS3UqW35NxuD1HWWrDSFpGEdYwjLliE0xCFORtKrsifY3R5gb7BH6pPsHDv2mo1Bb8YgECMbHUvn6JxPkvUdQjYS2zatSAjVjJBUW48TFVBIpFrC0MMolp4W40TxsGO3-ua7E-tkjXwpz8IU_BDVghuOjNxf4wAPRbb7izQUAFiv7bdhwowhCAaKw5DaCAGPjg94zAUlG_om88FubbiGX6O9rzY67aAoCVhNq_lHm2zPUANw48jHh7iqWzFQGWDexQElxlTMY3-d7C9fYXcLxW9XwrdK0dvMrRv6axRRr18W-KYQ9wqErUTBa6jQ-QrEXQmCq7g5D3zN2-R72WXF9y6ntdlU1KKz39gk_2-f3iG3lriaNoqBcJesydE9csMv09ndJ9-aYQTvtEM76Wc5pId55ux8T4ECbqeAg2lvMYK_bJDRNKG98WCSfhwvJpjWCAL8xflXtsMuzn_ARTofjHImrE916uP61-JMxrQLKIAGc3CvuAJJu7I4M5LX5i-iYQpdCDdlRsWCNoYx5lOT2QPSbwbHfktdZqVQI9M2bVUkthdqYZJYURgJTzDHim0hXZsJITzXEHh218Kso5rUpOk4Ikl04QEst0LPjmP2kKyP0pF8RGgM-E5PEmnqAhyp47lJjLuWAAphbu9YtkL6pZXwcUE-wguaaYNzVBRHNXFUEy-VxJnLsQyUwTmohpeq4Yxr3D_iBg8U8jI3uarScHKKH_g5Fn_fecuNA8c5aO053FXIi9ImOagL95Kgm9JZxpHGH6RpnqGQjcvGWtWpFfDegoCAwFwh-lUe85fM9MjIMFXIh9xa_2j8Fdr-l6ZXZY__Yd1PyM2c3QN3H4ynZH06mclngF2n4nnuXX4Ctcl1Ww |
| link.rule.ids | 315,786,790,1382,27957,27958,46329,46753 |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwxV3ratswFBZdC-v-7D7mXTVoRwt1alu-ZmOQus6SpU0haVjHGMKyZQgNcchlJP1V2Avs315gT7BH6pPsHDvOmo1B_4xBIEY2OpbO0TmfJOs7hGwktm1akRCqGSGpth4nKqCQSLWEoYdRLD0txoniYdOudcx3J9bJCvlSnIXJ-SEWC244MjJ_jQMcF6R3f7GGAgJr1_06zJgxBsFIcRhyGyHi0fEBj7mgZUPfZD4Yrg3X8KvU99VKsx7kJQEraSX_aJPtGWpwjayB17CyeVlrwUFlgIHnR5QYUzGT_XWyP3-H3S2Uv72QvlXI3mZu2dBfo4xy-bLEN7m8VyBtKQ6uoUqnSyB3KQwuI-cs9FVvke9Fp-VfvJyWJmNRis5-45P8z716m9ycQ2taycfCHbIi-3fJul9ktLtHvlXDCF5qhzbTz7JHD7Pk2dm2AgXoTgEK0_asD3-j7oimCW0PusP042A2xMxGEOMvzr-yHXZx_gMu0mm3n5FhfSpTH5fAZmcypi0AAjSYgofFRUjakvmxkaw2fxb1UuhDuClHVMxopRdjSjU5uk861eDYr6nzxBRqZNqmrYrE9kItTBIrCiPhCeZYsS2kazMhhOcaAo_vWph4VJOaNB1HJIkuPEDmVujZccwekNV-2pcPCY0B4ulJIk1dgC91PDeJceMScCFM7x3LVkinMBM-yPlHeM40bXCOiuKoJo5q4oWSOHM5loEyOAfV8EI1nHGN-0fc4IFCXmY2t6g0HJ7iN36Oxd8333Kj4TiN2p7DXYW8KIySg7pwOwm6KZ2MODL5gzTNMxSycdlaF3VqOcK3ICYgNleIfpXH_Dk5PZIyjBXyITPXPxp_hbb_pemLskf_sO7nZL12fHjAD-rNxmNyIyP7wM0I4wlZHQ8n8ilA2bF4lrmanzqTeX0 |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwxV3ratswFBZdC93-7D7mXTVoRwt1alu-ZmOQOs6SdU1LsrCOMYRlyxAa4pDLSPqr7An2bw-wN9gj9Ul2jh1nzcagf8YgECMbHUvnHJ1PkvUdQjYS2zatSAjVjJBUW48TFVBIpFrC0MMolp4W40TxoGnXO-abY-t4hXwpzsLk_BCLBTf0jGy8RgcfxMnuL9JQAGDtht-ACTOGIHAUhyG1EQIeHR_wmAtKNvRN5oPd2nANv0qjqlaajSAvCVhJK_mHm2zPUIMrZM20mYGeUW0tKKgMsO_8hBJjKiayXyfV-TvsbqH87YX0rUL2NnPLhv4SZZTLFyW-yuW9AGlLYXANNTpdwrhLUXAZOGeRr3aDfC_6LP_g5aQ0GYtSdPobneT_7dSb5PocWNNK7gm3yIrs3yZX_SKf3R3yrRZG8E47tJl-lj16kKXOzjYVKAB3CkCYtmd9-Bt1RzRNaHvQHaYfB7Mh5jWCCH9-9pXtsPOzH3CRTrv9jArrU5n6uAA2O5UxbQEMoMEUxldcgqQtmR8ayWrzZ1EvhS6Em3JExYxWejEmVJOju6RTC975dXWelkKNTNu0VZHYXqiFSWJFYSQ8wRwrtoV0bSaE8FxD4OFdC9OOalKTpuOIJNGFB7jcCj07jtk9stpP-_I-oTEAPD1JpKkLGEkdz01i3LYEVAiTe8eyFdIprIQPcvYRnvNMG5yjojiqiaOaeKEkzlyOZaAMzkE1vFANZ1zj_iE3eKCQ55nJLSoNhyf4hZ9j8ffN19zYd5z9-p7DXYU8K2ySg7pwMwm6KZ2MOPL4gzTNMxSycdFYF3VqOb63ICIgMleIfpnH_Dk1PVIyjBXyIbPWPxp_ibb_pemLsgf_sO6nZP2oWuNvG839h-RaxvSBOxHGI7I6Hk7kY8CxY_EkG2h-AjEqeCw |
| 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=Facile%2C+Novel+Methodology+for+the+Synthesis+of+Spiro%5Bpyrrolidin-3%2C3%E2%80%B2-oxindoles%5D%3A+Catalyzed+Ring+Expansion+Reactions+of+Cyclopropanes+by+Aldimines&rft.jtitle=Angewandte+Chemie+International+Edition&rft.au=Alper%2C+Phil+B.&rft.au=Meyers%2C+Christiane&rft.au=Lerchner%2C+Andreas&rft.au=Siegel%2C+Dionicio+R.&rft.date=1999-11-02&rft.issn=1433-7851&rft.eissn=1521-3773&rft.volume=38&rft.issue=21&rft.spage=3186&rft.epage=3189&rft_id=info:doi/10.1002%2F%28SICI%291521-3773%2819991102%2938%3A21%3C3186%3A%3AAID-ANIE3186%3E3.0.CO%3B2-E&rft.externalDBID=n%2Fa&rft.externalDocID=10_1002__SICI_1521_3773_19991102_38_21_3186__AID_ANIE3186_3_0_CO_2_E |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1433-7851&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1433-7851&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1433-7851&client=summon |