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21.16.2 Method 2: Kinetic Resolution with Catalytic Amounts of a Chiral Promoter

DOI: 10.1055/sos-SD-121-00025

Seidel, D.Science of Synthesis Knowledge Updates, (20123432.

Due to the high nucleophilicity of amines, their kinetic resolution with catalytic amounts of small-molecule-based chiral promoters (Nu*) represents a particular challenge (Scheme 14). Unlike alcohols, many amines directly react with a range of acylating reagents under very mild conditions, making the intervention of a chiral nucleophilic catalyst difficult. The key to the successful realization of a catalytic enantioselective process lies in reducing the rate of the background reaction of the amine with the (achiral) bulk acylating reagent (k1) relative to the rate of the catalyzed process (k2 and k3). Several promising strategies have been reported.

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