Mechanism of the Sharpless Epoxidation Reaction: A DFT Study
Robert D. Bach,
H. Bernhard Schlegel
Abstract:The Sharpless reaction is an enantioselective epoxidation of prochiral allylic alcohols that employs a Ti(IV) catalyst formed from titanium tetra(isopropoxide), Ti(O-i-Pr) 4 , diethyl tartrate (DET), and the oxidizing agent tert-butyl hydroperoxide. The M06-2X DFT functional with the 6-311+G-(d,p) basis set has been employed to model the structures and energetics of the Sharpless epoxidation reaction. The monomeric tetracoordinate titanium(IV) diethyltartrate is thermodynamically strongly favored to dimerize, … Show more
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