Vanadium‐Catalyzed Asymmetric Epoxidation of Allylic Alcohols Mediated by (+)‐Norcamphor‐Derived Hydroperoxide | Zendy

Lattanzi Alessandra | Zendy; Piccirillo Sandro | Zendy; Scettri Arrigo | Zendy

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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)

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