ENANTIOSELECTIVE ACETALIZATION OF RACEMIC 1,3-ALKANEDIOLS WITH L-MENTHONE UNDER KINETICALLY CONTROLLED CONDITIONS

被引：9

作者：

HARADA, T

TANAKA, S

OKU, A

机构：

[1] Department of Chemistry, Kyoto Institute of Technology, Matsugasaki, Kyoto, 606, Sakyo-ky

来源：

TETRAHEDRON | 1992年 / 48卷 / 40期

关键词：

ACETALIZATION; L-MENTHONE; KINETIC CONTROL; 1,3-ALKANEDIOL; KINETIC RESOLUTION;

D O I：

10.1016/S0040-4020(01)89438-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Racemic 1,3-alkanediols (rac-1) undergo an enantioselective acetalization by treatment with l-menthone 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 % ee are obtained when the racemic diols are allowed Lo react with 1.5 equiv of enol silyl ether 10 under similar conditions.

引用

页码：8621 / 8630

页数：10

共 14 条

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