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Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroalkenes Catalyzed by a Simple trans-4-Hydroxyprolylamide

Claudio Palomo*, Silvia Vera, Antonia Mielgo, Enrique Gómez-Bengoa

*Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco. Apdo. 1072. 20080 San Sebastián, Spain, Email: claudio.palomoehu.es

C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. Int. Ed., 2006, 45, 5984-5987.

DOI: 10.1002/anie.200602207 (free Supporting Information)


Abstract

A simple organocatalyst provided access to Michael adducts of the addition of nitroalkenes to aldehydes with very high diastereo- and enantioselectivity and a broad range of β-substitution patterns. Almost equimolar amounts of the aldehyde donor can be employed.

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Key Words

Nitro Compounds, Michael Addition, Organocatalysis


ID: J06-Y2006-2910