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

José Manuel BotubolAres | Zendy; James R. Hanson | Zendy; Rosario HernándezGalán | Zendy; Isidro G. Collado | Zendy

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

Author(s) -

José Manuel BotubolAres,

James R. Hanson,

Rosario HernándezGalán,

Isidro G. Collado

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00386

Subject(s) - allylic rearrangement , catalysis , chemistry , selectivity , substrate (aquarium) , manganese , titanium , reaction mechanism , reaction conditions , primary (astronomy) , organic chemistry , combinatorial chemistry , oceanography , physics , astronomy , geology

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.

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