A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates.
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.
Lowe
Jason T
JT
Department of Chemistry and Center for Chemical Methodology and Library Development, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Youngsaye
Willmen
W
Panek
James S
JS
D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D012821:Silanes