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Org Lett. 2003 Jan 9;5(1):79-80.

First synthesis of a beta(2)-homoamino acid by enantioselective catalysis.

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  • 1Faculty of Chemistry, University of Bielefeld, PO Box 10 01 31, D-33501 Bielefeld, Germany.

Abstract

The enantioselective conjugate addition of diethylzinc to the activated nitroolefin methyl 3-nitropropenoate is efficiently catalyzed by copper(I) complexes with BINOL-based enantiopure phosphoramidite ligands. The nitroolefin moiety acts as the predominant Michael acceptor, giving rise to the unambiguous formation of 2-alkyl-3-nitro-propanoates. Moderate to excellent enantioselectivities and high chemical yields are obtained. The product can easily be transformed into a beta(2)-homoamino acid. [reaction--see text]

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