Direct conversion of β-hydroxyketones to cyclic disiloxanes

GW O'Neil, MM Miller, KP Carter

Index: O'Neil, Gregory W.; Miller, Michael M.; Carter, Kyle P. Organic Letters, 2010 , vol. 12, # 22 p. 5350 - 5353

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Citation Number: 8

Abstract

β-Hydroxyketones can be directly converted to cyclic disiloxanes using diphenylchlorosilane in the presence of imidazole and an amine base. The reaction is proposed to proceed via a nucleophilic activation mechanism through a cyclic chairlike transition state affording hydrosilylated products with high diastereoselectivity.