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Synfacts 2005(2): 0219-0219  
DOI: 10.1055/s-2005-916074
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective β-Dicarbonyl Addition to Conjugated Nitroalkenes

Contributor(s): Mark Lautens, Andrew Martins
D. A. Evans*, D. Seidel
Harvard University, Cambridge, USA
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

There are numerous examples of enantioselective addition of β-dicarbonyl compounds to conjugated nitroalkenes. Many of these examples require long reaction time, low temperatures, or labile catalyst systems. This communication reports a highly enantioselective Michael ­addition of a wide variety of β-dicarbonyl compounds to a variety of conjugated nitroalkenes at ambient temperatures, with an air-stable catalyst of low loading, and under essentially neutral conditions.