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. 2010 Jul 14;132(27):9286-8.
doi: 10.1021/ja103618r.

Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway

Adam R Brown  1 , Wen-Hsin Kuo, Eric N Jacobsen
Affiliations

Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway

Adam R Brown et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1
Hydrogen-Bond Catalysis by Anion Binding
Scheme 2
Scheme 2
Possible Electrophile Activation Modes
See this image and copyright information in PMC

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