Asymmetric Baeyer-Villiger reaction: Diastereodifferentiating peracid oxidation of chiral acetal in the presence of Lewis acid

被引：35
|
作者：
Sugimura, T
Fujiwara, Y
Tai, A
机构：
[1] Faculty of Science, Himeji Institute of Technology, Ako-gun, Hyogo 678-12, Kanaji, Kamigori
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 34期
关键词：
D O I：
10.1016/S0040-4039(97)01338-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxidation of 2 with m-chloroperbenzoic acid in the presence of SnCl4 at -78 degrees C followed by hydrolysis afforded optically active 4 in a quantitative yield. The enantiomeric excess tee) of 4 largely depended on the reaction solvent, the chiral diol part, the Lewis acid and its amount. The best ee was 89% when 2 (R = Ph) having 2,4-pentanediol was oxidized at -100 degrees C. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：6019 / 6022
页数：4
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