Resolution of Terminal 1,2-Diols via Silyl Transfer

被引：19
|
作者：
Sun, Xixi [1 ]
Worthy, Amanda D. [1 ]
Tan, Kian L. [1 ]
机构：
[1] Boston Coll, Chestnut Hill, MA 02467 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期
关键词：
CATALYTIC ENANTIOSELECTIVE SILYLATION; HYDROLYTIC KINETIC RESOLUTION; SECONDARY ALCOHOLS; ASYMMETRIC DIHYDROXYLATION; CARBOHYDRATE-DERIVATIVES; REGIOSELECTIVE REACTIONS; EPOXIDES; INTRAMOLECULARITY; DESYMMETRIZATION; HYDROAMINATION;
D O I：
10.1021/jo4012909
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Through kinetic analysis and optimization, we report an improved resolution of terminal 1,2-diols via asymmetric silyl transfer. Because the reaction is a regiodivergent resolution, the monoprotected product could be isolated in excess of 95:5 er and 40% yield. The described method offers a means of chemically differentiating a terminal 1,2-diol with concomitant resolution of the enantiomers.
引用
收藏
页码：10494 / 10499
页数：6
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