THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF CIS-FUSED CYCLOPENTENO-1,2,4-TRIOXANES

被引：6
|
作者：
JEFFORD, CW
MISRA, D
DISHINGTON, AP
TIMARI, G
ROSSIER, JC
BERNARDINELLI, G
机构：
[1] Department of Organic Chemistry, University of Geneva
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 34期
关键词：
KINETIC RESOLUTION; DOUBLE DIASTEREOSELECTIVITY; 1,2-DIOL; DICAMPHANATES; X-RAY;
D O I：
10.1016/S0040-4039(00)73410-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Submission of racemic, cis-fused cyclopenteno-1,2,4-trioxanes (1 and 1-ent) to catalytic amounts of K2OsO4 and (DHQD)(2)PHAL and 1.2 equivalents of N-methylmorpholine N-oxide in aqueous acetone at 20 degrees C (hybrid AD-mix-beta) for 2 h gave the (-)-enantiomer, 1-ent (ee 95%) in 30% yield. The same reaction, but with (DHQ)(2)PHAL, (hybrid AD-mix-alpha) afforded the (+)-enantiomer, 1 (ee 95%) in 25% yield after 2.7 h reaction. Similar, efficient kinetic resolution of the racemic di-p-fluoro analogues (2 and 2-ent) was also achieved with the same reagents.
引用
收藏
页码：6275 / 6278
页数：4
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