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

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 unamb...

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Bibliographic Details
Published in:Organic letters 2003-01, Vol.5 (1), p.79-80
Main Authors: Rimkus, Audrius, Sewald, Norbert
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Copper - chemistry
Isomerism
Molecular Structure
Online Access:Get full text
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Summary: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]
ISSN:1523-7060
DOI:10.1021/ol027252k