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An Efficient Organocatalytic Method for Highly Enantioselective Michael Addition of Malonates to Enones Catalyzed by Readily Accessible Primary Amine-Thiourea

Krzysztof Dudziński, Anna M. Pakulska and Piotr Kwiatkowski*

*Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland, Email: pkwiatchem.uw.edu.pl

K. Dudziński, A. M. Pakulska, P. Kwiatkowski, Org. Lett., 2012, 14, 4222-4225.

DOI: 10.1021/ol3019055


Abstract

A practical and highly enantioselective Michael addition of malonates to enones to yield 1,5-ketoesters with good yields and excellent enantioselectivities is catalyzed by a simple and readily available bifunctional primary amine-thiourea derived from 1,2-diaminocyclohexane. The addition of weak acids and elevated temperature improved the efficiency of the reaction. This approach is applicable in multigram scale synthesis.

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Key Words

1,4-addition, organocatalysis


ID: J54-Y2012-2610