Enantioselective catalytic α-alkylation of aldehydes via an SN1 pathway

AR Brown, WH Kuo, EN Jacobsen

Index: Brown, Adam R.; Kuo, Wen-Hsin; Jacobsen, Eric N. Journal of the American Chemical Society, 2010 , vol. 132, # 27 p. 9286 - 9288

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Citation Number: 136

Abstract

Primary aminothiourea derivatives are shown to catalyze enantioselective alkylation of α- arylpriopionaldehdyes with diarylbromomethane. Evidence for a stepwise, SN1 mechanism in the substitution reaction induced by anion binding to the catalyst is provided by catalyst structure− activity studies, kinetic isotope effects, linear free-energy relationship studies, and competition experiments.

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