Enantioselective Syntheses of 2‑Azabicyclo[2.2.1]heptanes via Brønsted Acid Catalyzed Ring-Opening of meso-Epoxides

A chiral phosphoric acid-catalyzed ring-opening of meso-epoxides was developed. A range of 2-azabicyclo[2.2.1]­heptanes were obtained in high yields with excellent enantioselectivities. In addition, the hydroxyl and amide groups in the products provided handles for further derivatization.

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (48), p.8791-8795
Main Authors: Cai, Min, Ma, Jiao, Wu, Qimin, Lin, Aijun, Yao, Hequan
Format: Article
Language:English
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Summary:A chiral phosphoric acid-catalyzed ring-opening of meso-epoxides was developed. A range of 2-azabicyclo[2.2.1]­heptanes were obtained in high yields with excellent enantioselectivities. In addition, the hydroxyl and amide groups in the products provided handles for further derivatization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03529