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Synthesis 2005(19): 3263-3270  
DOI: 10.1055/s-2005-918481
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Quaternary α-Hydroxy Acids by Alkylation of α-Ketoamide-Derived Dienediolates

Rebecca Newton, Stephen P. Marsden*
School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK
Fax: +44(113)3436565; e-Mail: s.p.marsden@leeds.ac.uk;
Further Information

Publication History

Received 6 September 2005
Publication Date:
14 November 2005 (online)

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Abstract

Double deprotonation of α-ketoamides generates dienediolates, which undergo regioselective α-alkylation to yield α-substituted-α-hydroxy-β,γ-unsaturated amides. 1,2-Disubstituted al­kenes are generated exclusively as the E-isomer. 1,1-Disubstituted and 1,1,2-trisubstituted olefins can also be prepared. The amides can be readily converted to the corresponding acids.

Key words

ketoamides - alkylations - dianions - hydroxy acids - stereoselective­ olefin synthesis