A protocol for the asymmetric epoxidation of allylic alcohols has been established that employs VO(acac)(2) as catalyst, the commercial achiral hydroxamic acid, N-hydroxy-N-phenyl-benzamide, and optically pure (+)-norcamphor-derived hydroperoxide as oxygen atom donor and chiral source. Variation of the reaction parameters has a significant effect on the level of asymmetric induction. Under optimized conditions, the epoxy alcohols have been isolated in good yields with up to 67% ee and complete control of the diastereoselectivity.
Vanadium-catalyzed asymmetric epoxidation of allylic alcohols mdiated by (+)-norcamphor derived hydroperoxide
LATTANZI, Alessandra;SCETTRI, Arrigo
2005-01-01
Abstract
A protocol for the asymmetric epoxidation of allylic alcohols has been established that employs VO(acac)(2) as catalyst, the commercial achiral hydroxamic acid, N-hydroxy-N-phenyl-benzamide, and optically pure (+)-norcamphor-derived hydroperoxide as oxygen atom donor and chiral source. Variation of the reaction parameters has a significant effect on the level of asymmetric induction. Under optimized conditions, the epoxy alcohols have been isolated in good yields with up to 67% ee and complete control of the diastereoselectivity.File in questo prodotto:
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