Tetrahedron Letters

The first asymmetric synthesis of a 4-aryl-substituted 5-carboxy-3, 4-dihydropyridin-2-one derivative

X Huang, J Zhu, S Broadbent

Index: Huang, Xiaojun; Zhu, Jiang; Broadbent, Scott Tetrahedron Letters, 2010 , vol. 51, # 12 p. 1554 - 1557

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Citation Number: 23

Abstract

A simple and practical route for the asymmetric synthesis of (S)-4-(4-fluorophenyl)-1, 4, 5, 6- tetrahydro-6-oxo-3-pyridinecarboxylic acid (1) is presented. The procedure comprises catalytic desymmetrization of a meso-anhydride using a chiral thiourea organocatalyst, followed by selective formylation and cyclization.