Journal of the American Chemical Society, Vol.132, No.27, 9286-9288, 2010
Enantioselective Catalytic alpha-Alkylation of Aldehydes via an S(N)1 Pathway
Primary aminothiourea derivatives are shown to catalyze enantioselective alkylation of alpha-arylpriopionaldehdyes with diarylbromomethane. Evidence for a stepwise, S(N)1 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.