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Synlett 2004(11): 1957-1960
DOI: 10.1055/s-2004-830887
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
Further Information
Publication History
Received
2 June 2004
Publication Date:
04 August 2004 (online)


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.
Key Words
conjugate addition - three component coupling - oligomerisation - piperidin-2-one