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....

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Published inAngewandte Chemie (International ed.) Vol. 38; no. 21; pp. 3186 - 3189
Main Authors Alper, Phil B., Meyers, Christiane, Lerchner, Andreas, Siegel, Dionicio R., Carreira, Erick M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 02.11.1999
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Alkaloids
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cyclopropanes
Iodides
Lewis acid
Magnesium
Methodology
Nucleophilic additions
Organic compounds
Physical Sciences
Ring expansions
Science & Technology
Spiro compounds
Synthesis
ORGANIC-SYNTHESIS
ASYMMETRIC-SYNTHESIS
STEREOCONTROLLED TOTAL SYNTHESIS
ring expansions
alkaloids
cyclopropanes
nucleophilic additions
spiro compounds
DERIVATIVES
(+/-)-GELSEMINE
EFFICIENT
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Summary: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.
Bibliography:ark:/67375/WNG-2K77KHB7-8
ArticleID:ANIE3186
istex:272C3DC9553EC888D5488AD3B43C2BE0A451F638
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.0.CO;2-E