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Synfacts 2009(10): 1163-1163
DOI: 10.1055/s-0029-1217947
DOI: 10.1055/s-0029-1217947
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective α-Nitroalkylation of Aldehydes Using SOMO Catalysis
J. E. Wilson, A. D. Casarez, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
Further Information
Publication History
Publication Date:
22 September 2009 (online)
Significance
The enantioselective α-nitroalkylation of aldehydes was achieved by reacting enolizable aldehydes with silyl nitronates in the presence of imidazolidinone catalyst 1 under oxidative conditions. The corresponding β-nitroaldehydes were obtained in good yields (up to 95%) and high enantioselectivities (er up to 98.5:1.5). The diastereoselectivity was controlled by simple variation of the reaction conditions and the nitronate. Two reasonable mechanistic scenarios for the formation of both diastereoisomers are proposed.