Lowe Jason T, Youngsaye Willmen, Panek James S
Department of Chemistry and Center for Chemical Methodology and Library Development, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
J Org Chem. 2006 Apr 28;71(9):3639-42. doi: 10.1021/jo060134g.
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.
描述了一种多克规模的、具有高对映体纯度的3-硅烷基缩水甘油酸甲酯（环氧硅烷）四种立体异构体的合成方法。关键反应包括反式乙烯基硅烷的夏普莱斯不对称环氧化反应（SAE）和外消旋顺式环氧硅烷的酶促拆分反应，以建立所需的构型。纯化过程只需很少的色谱分离步骤（13步中有5步），为反式和顺式异构体都建立了方便的反应序列。
