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Communication | Special issue | Vol 74, No. 1, 2007, pp.191-197
Published online, 2nd October, 2007
DOI: 10.3987/COM-07-S(W)48
An Alternative Regioselective Ring-Opening of Epoxides to Chlorohydrins Mediated by Chlorotitanium(IV) Reagents

Kiyoshi Nishitani,* Kyoko Shinyama, and Koji Yamakawa

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

A regioselective cleavage of various epoxides to vic-chlorohydrin isomers by using TiCl4 or TiCl4-Ti(O-i-Pr)4 complex was investigated. The less substituted alcohols, C2-attack products, were formed by the use of TiCl4 in CH2Cl2. On the other hand, the less substituted chlorides, C1-attack products, were formed by using TiCl(O-i-Pr)3 in DMF. These regioselectivities depend on both the acidity of the Lewis acids and the polarity of the solvents.