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
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.
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页码:8621 / 8630
页数:10
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