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Oxidative Rearrangement of Cyclic Tertiary Allylic Alcohols with IBX in DMSO

Masatoshi Shibuya, Shinichiro Ito, Michiyasu Takahashi and Yoshiharu Iwabuchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan, Email: iwabuchimail.pharm.tohoku.ac.jp

M. Shibuya, S. Ito, M. Takahashi, Y. Iwabuchi, Org. Lett., 2004, 6, 4303-4306.

DOI: 10.1021/ol048210u (free Supporting Information)


Abstract

A practical and environmentally friendly method for the oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to α,β-unsaturated β-disubstituted ketones by IBX in DMSO is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are tolerated.

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Key Words

IBX, Oxidation (Alkenes, Alcohols), Enones, Oxidative Rearrangement


ID: J54-Y2004-980