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

Authors :
Qinghe Liu
Taige Kong
Chuanfa Ni
Jinbo Hu
Source :
Organic Letters. 24:5982-5987
Publication Year :
2022
Publisher :
American Chemical Society (ACS), 2022.

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.

Details

ISSN :
15237052 and 15237060
Volume :
24
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....f2b493bbe0e92f56a492931d6df2719f