Synlett 2004(11): 1957-1960  
DOI: 10.1055/s-2004-830887
LETTER
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of 3,4,5,6-Tetrasubstituted Piperidin-2-ones by Three-Component Coupling

Stephen G. Davies*a, Andrew D. Smitha, Andrew R. Cowleyb
a Department of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
b Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
e-Mail: steve.davies@chem.ox.ac.uk;
Further Information

Publication History

Received 2 June 2004
Publication Date:
04 August 2004 (online)

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Abstract

The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.