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

ABSTRACT: 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.

SUBMITTER: Botubol-Ares JM 

PROVIDER: S-EPMC6641598 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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

Botubol-Ares José Manuel JM   Hanson James R JR   Hernández-Galán Rosario R   Collado Isidro G IG  

ACS omega 20170703 7

A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using <i>tert</i>-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. ...[more]

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