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Issue 41, 2012

Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates

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Abstract

The asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates has been developed. Various 5-substituted 3-pyrrolidin-2-ones were obtained in high yields (up to 93%) with excellent stereoselectivities (up to 94% ee, 95 : 5 dr), using a novel bifunctional C1-symmetric guanidine organocatalyst embodied a secondary amine subunit.

Graphical abstract: Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates

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Article information


Submitted
28 Feb 2012
Accepted
21 Mar 2012
First published
21 Mar 2012

Chem. Commun., 2012,48, 5040-5042
Article type
Communication

Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates

Y. Yang, S. Dong, X. Liu, L. Lin and X. Feng, Chem. Commun., 2012, 48, 5040 DOI: 10.1039/C2CC31470C

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