Tetrahedron

Synthesis of α-silylalkylbenzoxazoles and oxazoles from stable silylketenes

SP Marsden, JT Steer, BS Orlek

Index: Marsden, Stephen P.; Steer, James T.; Orlek, Barry S. Tetrahedron, 2009 , vol. 65, # 28 p. 5503 - 5512

Full Text: HTML

Citation Number: 7

Abstract

Stable silylketenes, prepared by rhodium-catalysed decomposition of silyldiazoketones, undergo addition/cyclocondensation sequences with aminophenols and aminomalonate to give α-silylalkylbenzoxazoles and oxazoles, respectively. The silicon can be retained throughout functional group interconversions or can be removed by protodesilylation under acidic conditions as desired.