Abstract
Abstract The migratory aptitude of the Lewis acid-promoted epoxide rearrangement has been studied with exceptionally bulky, Lewis acidic methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR). With α,α-disubstituted epoxides, the organoaluminum-promoted epoxide rearrangement is interpreted for by proceeding with rigorous migration of hydride syn to the less hindered site of the epoxide ring, while the facile anti migration of the alkyl groups has been observed in tri- and tetrasubstituted epoxides. The selectivity observed in various types of epoxides is found to be far superior to that with other ordinary Lewis acids such as BF3·OEt2 and SnCl4.
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