American Chemical Society
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Enantioselective Catalytic α-Alkylation of Aldehydes via an SN1 Pathway

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journal contribution
posted on 2010-07-14, 00:00 authored by Adam R. Brown, Wen-Hsin Kuo, Eric N. Jacobsen
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.