Mild Epoxidation of Allylic Alcohols Catalyzed by Titanium(III) Complexes: Selectivity and Mechanism

A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using tert-butyl hydroperoxide as oxidant and Ti­(III) species generated by reduction of Ti­(IV) complexes, with manganese (0) in 1,4-dioxane under mild reaction conditions. The...

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Bibliographic Details
Published in:ACS omega 2017-07, Vol.2 (7), p.3083-3090
Main Authors: Botubol-Ares, José Manuel, Hanson, James R, Hernández-Galán, Rosario, Collado, Isidro G
Format: Article
Language:English
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Summary:A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using tert-butyl hydroperoxide as oxidant and Ti­(III) species generated by reduction of Ti­(IV) complexes, with manganese (0) in 1,4-dioxane under mild reaction conditions. The reaction proceeded with wide substrate scope and high chemo- and diastereoselectivity. A mechanistic pathway for the reaction is also discussed.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.7b00386