Highly enantioselective organocatalytic sulfa-Michael addition to α,β-unsaturated ketones

Rana, Nirmal K. ; Selvakumar, Sermadurai ; Singh, Vinod K. (2010) Highly enantioselective organocatalytic sulfa-Michael addition to α,β-unsaturated ketones The Journal of Organic Chemistry, 75 (6). pp. 2089-2091. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo902634a

Related URL: http://dx.doi.org/10.1021/jo902634a

Abstract

A cinchona alkaloid-derived urea was found to be an efficient organocatalyst for catalyzing enantioselective conjugate addition between thiols and various α,β-unsaturated ketones to provide optically active sulfides with high chemical yields (up to >99%) and enantiomeric excess (up to >99% ee). The reaction was performed with 0.1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:55446
Deposited On:18 Aug 2011 08:49
Last Modified:18 Aug 2011 08:49

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