INDIUM(III) CHLORIDE-PROMOTED REARRANGEMENT OF EPOXIDES - A SELECTIVESYNTHESIS OF SUBSTITUTED BENZYLIC ALDEHYDES AND KETONES

A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxi des isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are sim ple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with sev eral acid-sensitive functionalities. This protocol provides a highly s elective synthesis of substituted benzylic aldehydes and ketones. Howe ver, rearrangement of alkyl-substituted epoxides is not very selective .