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Dynamic Kinetic Resolution-Enabled Highly Stereoselective Nucleophilic Fluoroalkylation to Access Chiral β-Fluoro Amines.

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β-Fluorinated amine is highly desirable for biological and pharmaceutical science, because replacing a C-H bond with a C-F bond can change the physical and chemical properties of the parent molecule… Click to show full abstract

β-Fluorinated amine is highly desirable for biological and pharmaceutical science, because replacing a C-H bond with a C-F bond can change the physical and chemical properties of the parent molecule to a large extent but not significantly alter its overall geometry. Herein, the highly stereoselective nucleophilic monofluoromethylation of imines have been developed. It is proposed that the chelated transition state enables the chiral induction by the dynamic kinetic resolution of the chiral α-fluoro carbanions.

Keywords: highly stereoselective; stereoselective nucleophilic; chiral fluoro; dynamic kinetic; kinetic resolution

Journal Title: Organic letters
Year Published: 2022

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