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Oxidative Rearrangement of Tertiary Allylic Alcohols Employing Oxoammonium Salts

Masatoshi Shibuya, Masaki Tomizawa and Yoshiharu Iwabuchi*

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

M. Shibuya, M. Tomizawa, Y. Iwabuchi, J. Org. Chem., 2008, 73, 4750-4752.

DOI: 10.1021/jo800634r (free Supporting Information)



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Abstract

Oxoammonium salts enable a practical and highly efficient oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds. Acyclic substrates as well as medium membered ring substrates and macrocyclic substrates can be oxidized.

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Key Words

Enones, TEMPO-Derivatives


ID: J42-Y2008-1660