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Enantioenriched 1,4-Benzoxazepines via Chiral Bronsted Acid-Catalyzed Enantioselective Desymmetrization of 3-Substituted Oxetanes.

ABSTRACT: Herein, we present a highly enantioselective desymmetrization of 3-substituted oxetanes enabled by a confined chiral phosphoric acid. This metal-free process allows effective access to chiral seven-membered 1,4-benzoxazepines with a high degree of enantiocontrol, under mild reaction conditions. The developed synthetic strategy tolerates a broad substrate scope and demonstrates its synthetic utility in various enantioselective product transformations, thus proving its effectiveness in diverse scenarios.

SUBMITTER: Nigrini M

PROVIDER: S-EPMC10729023 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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Enantioenriched 1,4-Benzoxazepines via Chiral Brønsted Acid-Catalyzed Enantioselective Desymmetrization of 3-Substituted Oxetanes.

Nigríni Martin M Bhosale Viraj A VA Císařová Ivana I Veselý Jan J

The Journal of organic chemistry 20231121 24

Herein, we present a highly enantioselective desymmetrization of 3-substituted oxetanes enabled by a confined chiral phosphoric acid. This metal-free process allows effective access to chiral seven-membered 1,4-benzoxazepines with a high degree of enantiocontrol, under mild reaction conditions. The developed synthetic strategy tolerates a broad substrate scope and demonstrates its synthetic utility in various enantioselective product transformations, thus proving its effectiveness in diverse sce ...[more]

PMID: 37987742

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