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Nickel-Catalyzed Enantio- and Diastereoselective Synthesis of Fluorine-Containing Vicinal Stereogenic Centers.

ABSTRACT: The construction of fluorinated architectures has been a topic of interest to medicinal chemists due to their unique ability to improve the pharmacokinetic properties of bioactive compounds. However, the stereoselective synthesis of fluoro-organic compounds with vicinal stereogenic centers is a challenge. Herein, we present a directing-groupfree nickel-hydride catalyzed hydroalkylation of fluoroalkenes to afford fluorinated motifs with two adjacent chiral centers in excellent yields and stereoselectivities. Our method provides expedient access to biologically relevant, highly enantioenriched organofluorine compounds. Furthermore, the strategy can be used for the diastereo- and enantioselective synthesis of vicinal difluorides, which have recently gained attention in the fields of organocatalysis and peptide mimics.

SUBMITTER: Dhawa U

PROVIDER: S-EPMC11363326 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Enantio- and Diastereoselective Synthesis of Fluorine-Containing Vicinal Stereogenic Centers.

Dhawa Uttam U Lavrencic Lara L Hu Xile X

ACS central science 20240817 8

The construction of fluorinated architectures has been a topic of interest to medicinal chemists due to their unique ability to improve the pharmacokinetic properties of bioactive compounds. However, the stereoselective synthesis of fluoro-organic compounds with vicinal stereogenic centers is a challenge. Herein, we present a directing-groupfree nickel-hydride catalyzed hydroalkylation of fluoroalkenes to afford fluorinated motifs with two adjacent chiral centers in excellent yields and stereose ...[more]

PMID: 39220696

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