Tetrahedron: Asymmetry

Enantioselective synthesis of unsaturated α-hydroxy acids

JA Macritchie, A Silcock, CL Willis

Index: Macritchie, Jacqueline A.; Silcock, Alan; Willis, Christine L. Tetrahedron Asymmetry, 1997 , vol. 8, # 23 p. 3895 - 3902

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Citation Number: 56

Abstract

(S)-and (R)-2-Hydroxyhex-5-enoic acid and (S)-and (R)-2-hydroxyhept-6-enoic acid were prepared in excellent yields and enantiomeric excesses (> 99% ee) from the corresponding α-keto esters by the enzyme catalysed hydrolysis of the ester and reduction of the ketone in a single pot process. The enantioselective synthesis of (S)-2-hydroxypent-4-enoic acid was achieved via reaction of the reagent derived from allyl bromide and indium metal with the ...