Facile Conversion of Epoxides to Chlorohydrins with Titanium(IV) Chloride/ 1,8-Diazabicyclo[5.4.0]undec-7-ene

Abstract

A series of epoxides has been converted to the analogous chlorohydrins by treatment with titanium(IV) chloride and 1,8-diazabicyclo[5.4.0-undec-7-ene. This procedure tolerates acetal protecting groups normally labile to aqueous acids, and, when used in conjunction with the Sharpless epoxidation protocols, it allows the preparation of chiral chlorodiols selectively protected at one hydroxy group.