Organic letters

Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO

M Shibuya, S Ito, M Takahashi, Y Iwabuchi

Index: Shibuya, Masatoshi; Ito, Shinichiro; Takahashi, Michiyasu; Iwabuchi, Yoshiharu Organic Letters, 2004 , vol. 6, # 23 p. 4303 - 4306

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Citation Number: 68

Abstract

A practical and environmentally friendly method for oxidative rearrangement of five-and six- membered cyclic tertiary allylic alcohols to β-disubstituted α, β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (eg, Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.