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Catalytic Asymmetric Michael Reactions of Acetaldehyde

Authors


  • We thank Jutta Rosentreter for technical assistance. Generous support by the Max-Planck-Society, the DFG (SPP 1179, Organokatalyse), Novartis (Young Investigator Award to B.L.), AstraZeneca (Award in Organic Chemistry to B.L.), Secretaría de Estado de Universidades e Investigación del Ministerio de Educación y Ciencia (Fellowship to P.G.G.), and the Fonds der Chemischen Industrie is gratefully acknowledged.

Abstract

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Acetaldehyde, now a big contender: A silyl prolinol derivative was found to catalyze the first Michael addition of acetaldehyde with both aromatic and aliphatic nitroolefins in excellent enantioselectivities (see scheme, TMS=trimethylsilyl). The utility of the reaction is illustrated in the synthesis of three current pharmaceuticals and in the synthesis of an enantiopure 3-monosubstituted pyrrolidine.

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