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Synfacts 2007(5): 0538-0538  
DOI: 10.1055/s-2007-968402
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

A Water-Compatible Catalyst for the Michael Reaction of Ketones to Nitroolefins

Contributor(s): Benjamin List, Subhas Chandra Pan
Vishnumaya, V. K. Singh
Indian Institute of Technology Kanpur, India
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

A new diamine catalyst has been developed for the asymmetric Michael reaction of cyclic ketones to nitroolefins. The catalyst is water-compatible and highly effective for the Michael reaction with nitroolefins when used in combination with TFA. With 10 mol% of catalyst 1 moderate to high diastereoselectivities (dr = 77:23 to 98:2) and enantioselectivities (er = 87:13 to 99.5:0.5) are obtained for different aromatic and hetero­aromatic nitroolefins. A non-aromatic cyclohexyl nitroolefin has also been used with high enantioselectivity (er = 94:6).