Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole

A new asymmetric organocatalytic synthesis of spirocyclopropane oxindoles has been developed. The method is based on the Michael addition of N‐Boc‐protected 3‐chlorooxindole to unsaturated 1,4‐dicarbonyl compounds, affording trans‐substituted spirocyclopropane oxindole derivatives in high diastereo‐...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-06, Vol.2014 (17), p.3599-3606
Main Authors: Ošeka, Maksim, Noole, Artur, Žari, Sergei, Öeren, Mario, Järving, Ivar, Lopp, Margus, Kanger, Tõnis
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Cyclization
Michael addition
Organocatalysis
Small ring systems
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Summary:A new asymmetric organocatalytic synthesis of spirocyclopropane oxindoles has been developed. The method is based on the Michael addition of N‐Boc‐protected 3‐chlorooxindole to unsaturated 1,4‐dicarbonyl compounds, affording trans‐substituted spirocyclopropane oxindole derivatives in high diastereo‐ and enantioselectivity. Symmetrically substituted trans‐isomers of spirocyclopropane oxindole were obtained in high ee through asymmetric organocatalysis, whereas the racemic cis‐isomer was only formed as a minor product.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402061