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Communication | Special issue | Vol 67, No. 2, 2006, pp.555-559
Published online, 30th September, 2005
DOI: 10.3987/COM-05-S(T)70
An Enantiocontrolled Approach for the Synthesis of Chiral 3,5-Disubstituted 2(1H)-pyridinones

David R. Williams,* David C. Kammler, and William R. F. Goundry

*Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.

Abstract

An enantioselective route for the convergent synthesis of chiral, nonracemic 5-substituted 3-acyl-2(1H)-pyridinones is reported. Claisen rearrangement provides direct access to the α-branched 2-[4-(tert-butyldimethylsilanoxy)cyclohex-2-enyl]-3-hydroxypropionaldehyde as a key intermediate. The application of mild oxidation conditions facilitates the preparation of a series of 3,5-disubstituted 2(1H)-pyridinones.