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Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines.

Authors :
Wang ZH
Wu ZJ
Yue DF
You Y
Xu XY
Zhang XM
Yuan WC
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2016 Jul 06; Vol. 14 (27), pp. 6568-76.
Publication Year :
2016

Abstract

An organocatalyzed direct asymmetric vinylogous Michael addition reaction of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines has been developed with a chiral bifunctional amine-squaramide as the catalyst. This approach provides easy access to a series of optically active α,β-unsaturated γ-substituted butyrolactams in high yields (up to 99%) with excellent diastereoselectivities (up to >99 : 1) and enantioselectivities (up to >99% ee).

Details

Language :
English
ISSN :
1477-0539
Volume :
14
Issue :
27
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
27304088
Full Text :
https://doi.org/10.1039/c6ob01191h