First Synthesis of a β2-Homoamino Acid by Enantioselective Catalysis
- 10 December 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (1) , 79-80
- https://doi.org/10.1021/ol027252k
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 β2-homoamino acid.Keywords
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