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Vanadium‐Catalyzed Asymmetric Epoxidation of Allylic Alcohols Mediated by (+)‐Norcamphor‐Derived Hydroperoxide
Author(s) -
Lattanzi Alessandra,
Piccirillo Sandro,
Scettri Arrigo
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400736
Subject(s) - chemistry , allylic rearrangement , catalysis , asymmetric induction , stereoselectivity , enantioselective synthesis , vanadium , organic chemistry , hydroxamic acid , medicinal chemistry
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 ‐phenylbenzamide, 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)