Tetrahedron

Enantioselective acetalization of racemic 1, 3-alkanediols with l-methone under kinetically controlled conditions

T Harada, S Tanaka, A Oku

Index: Harada, Toshiro; Tanaka, Sachi; Oku, Akira Tetrahedron, 1992 ,  vol. 48,  # 40  p. 8621 - 8630

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Citation Number: 10

Abstract

Racemic 1, 3-alkanediols (rac-1) undergo an enantioselective acetalization by treatment with l-methone enol trimethylsilyl ether (10) in the presence of trifluoromethanesulfonic acid (10 mol%) to give thermodynamically less stable spiroacetal 3 (derived from 1) in preference to spiroacetal 4 (derived from ent-1). The kinetically controlled acetalization is applied to a novel kinetic resolution of racemic 1, 3-alkanediols: Optically active diols ent-1 of 55–95% ...