A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates

被引：18
|
作者：
Lowe, JT
Youngsaye, W
Panek, JS
机构：
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 09期
关键词：
D O I：
10.1021/jo060134g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a racemic cis-epoxysilane to establish the desired configurations. Few chromatographic separations (5 columns out of 13 steps) are required for purification, establishing a convenient reaction sequence for both the trans- and cis-isomers.
引用
收藏
页码：3639 / 3642
页数：4
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