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Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

ABSTRACT: 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.

SUBMITTER: Brown AR

PROVIDER: S-EPMC2909636 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

Brown Adam R AR Kuo Wen-Hsin WH Jacobsen Eric N EN

Journal of the American Chemical Society 20100701 27

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. ...[more]

PMID: 20568761

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