KINETIC RESOLUTION IN THE ASYMMETRIC HYDROXYLATION OF ENOLATES - STEREOSPECIFIC SYNTHESIS OF (2S,3R)-(-)-VERRUCARINOLACTONE

被引：15
|
作者：
DAVIS, FA
KUMAR, A
机构：
[1] Department of Chemistry, Drexel University, Philadelphia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 12期
关键词：
D O I：
10.1021/jo00038a021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric hydroxylation of racemic 3-methylvalerolactone (1) with substoichiometric amounts of the (-)-(camphorylsulfonyl)oxaziridine 3a affords (2S,3R)-(-)-verrucarinolactone (2a) in 60% ee, which on crystallization is obtained enantiomerically pure. This result not only represents a highly efficient stereospecific synthesis of an important lactone, but also demonstrates the application of kinetic resolution and asymmetric hydroxylation in the synthesis of enantiomerically enriched alpha-hydroxy carbonyl compounds having multiple stereocenters.
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页码：3337 / 3339
页数：3
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