Sc(OTf)3 catalyzed [3 + 2]-annulation reaction of donor–acceptor aziridines with methylene exo-glycals: synthesis of chiral carbohydrate-spiro-heterocycles

文献情報

出版日 2021-03-10

DOI 10.1039/D1QO00228G

インパクトファクター 5.281

著者

Jie-Hui Zhang, Cheng-Lin Pan, Huan-Huan Zhang

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要旨

A Sc(OTf)3 catalyzed [3 + 2]-annulation reaction between donor–acceptor aziridines and several exo-glycals has been developed. Using this method, some exo-glycals derived from D-ribose, D-galactose and uridine can be converted into carbohydrate-spiro-heterocycles easily in good yields. Simple derivatization of the products gives proline analogues and polycyclic compounds. Moreover, this reaction disclosed the stereochemistry characteristic of the reaction between racemic D–A aziridines and chiral enolethers.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Sc(OTf)3 catalyzed [3 + 2]-annulation reaction of donor–acceptor aziridines with methylene exo-glycals: synthesis of chiral carbohydrate-spiro-heterocycles

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