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Review | Special issue | Vol 80, No. 1, 2010, pp.63-82
Published online, 12th March, 2009
DOI: 10.3987/REV-09-SR(S)1
■ A New Type of Oxidation-Reduction Condensation by the Combined Use of Phenyl Diphenylphosphinite and Oxidant

Teruaki Mukaiyama,* Kiichi Kuroda, and Yuji Maruyama

*Tokyo Chemical Industry Co., Ltd., 6-15-5 (TCI) Toshima, Kita-ku, Tokyo 114-0003, Japan

Abstract

A new type of oxidation−reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.