Highly Enantio- and Diastereoselective Generation of Two Quaternary Centers in Spirocyclopropanation of Oxindole Derivatives

Spirocyclopropanes: Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2‐chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-11, Vol.18 (47), p.14929-14933
Main Authors: Noole, Artur, Sucman, Natalia S., Kabeshov, Mikhail A., Kanger, Tõnis, Macaev, Fliur Z., Malkov, Andrei V.
Format: Article
Language:English
Subjects:
asymmetric catalysis
cascade reactions
Chemistry
cyclization
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
organocatalysis
spiro compounds
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:Spirocyclopropanes: Only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2‐chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high yield and high enantio‐ and diastereoselectivity (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201203099