Tetrahedron

Synthesis of α-(Alkoxysilyl) acetic esters. A route to 1, 2 diols

O Andrey, Y Landais, D Planchenault, V Weber

Index: Andrey, Olivier; Landais, Yannick; Planchenault, Denis; Weber, Valery Tetrahedron, 1995 , vol. 51, # 44 p. 12083 - 12096

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Citation Number: 28

Abstract

An easy route to α-(alkoxysilyl) acetic esters and their utilization is described. It involves a two-step sequence carried out in one pot: Rhodium catalyzed Si-H insertion of a carbenoid, generated by decomposition of N2CHCO2Et, followed by a nucleophilic attack onto the Si-Cl bond by an alcohol. Alkylation of the title esters, reduction of the ester function and finally oxidation of the C-Si bond provide a facile entry to 1, 2-diols.