Tetrahedron: Asymmetry

Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1, 3-benzodioxole-5-ethanol: an efficient resolution of chiral intermediates of the remarkable …

S Easwar, NP Argade

Index: Easwar, Srinivasan; Argade, Narshinha P. Tetrahedron Asymmetry, 2003 , vol. 14, # 3 p. 333 - 337

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Citation Number: 18

Abstract

(S)-(+)-α-Methyl-1, 3-benzodioxole-5-ethanol 5 is a chiral building block in the synthesis of the future drug (−)-talampanel 1. Amano PS-induced enantioselective acylation of (±)-3 at 50° C using vinyl acetate as acyl donor furnished (+)-5 in 53% yield and 80% ee, and the corresponding acetyl derivative (−)-(R)-α-methyl-1, 3-benzodioxole-5-ethyl acetate 6 in 44% yield and 96% ee The base-catalysed methanolysis of (−)-6 followed by Mitsunobu ...