A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates

JT Lowe, W Youngsaye, JS Panek

Index: Lowe, Jason T.; Youngsaye, Willmen; Panek, James S. Journal of Organic Chemistry, 2006 , vol. 71, # 9 p. 3639 - 3642

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Citation Number: 18

Abstract

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 ...

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