Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones
1998; American Chemical Society; Volume: 63; Issue: 23 Linguagem: Inglês
10.1021/jo980793w
ISSN1520-6904
AutoresBrindaban C. Ranu, Umasish Jana,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C−O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl-substituted epoxides is not very selective.
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