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Synfacts 2008(12): 1335-1335  
DOI: 10.1055/s-0028-1083575
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Michael Addition of Nitroalkanes to Nitroolefines

Contributor(s): Benjamin List, Steffen Müller
C. Rabalakos, W. D. Wulff*
Michigan State University, East Lansing, USA
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

An efficient method for the Michael addition of nitroalkanes to nitroalkenes, promoted by the new bifunctional catalyst 1 is reported. The desired 1,3-dinitro compounds were obtained in good yields (60-94%) and high enantioselectivities (er up to 97.5:2.5). A combination of a ­Brønsted-basic DMAP unit and an H-bond donating thiourea moiety, both attached to the privi­ledged chiral ­BINAM scaffold was found to provide a superb catalyst motif for the reported reaction.