Enantioselective enolate protonation in sulfa-Michael addition to α-substituted N-acryloyloxazolidin-2-ones with bifunctional organocatalyst

Rana, Nirmal K. ; Singh, Vinod K. (2011) Enantioselective enolate protonation in sulfa-Michael addition to α-substituted N-acryloyloxazolidin-2-ones with bifunctional organocatalyst Organic Letters, 13 (24). pp. 6520-6523. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol202808n

Related URL: http://dx.doi.org/10.1021/ol202808n

Abstract

Organocatalytic conjugate addition of thiols to α-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:89726
Deposited On:30 Apr 2012 14:31
Last Modified:30 Apr 2012 14:31

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