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

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 deriva...

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Published inOrganic chemistry frontiers an international journal of organic chemistry Vol. 8; no. 10; pp. 2203 - 2207
Main Authors Jie-Hui, Zhang, Cheng-Lin, Pan, Zhang, Huan-Huan, Peng-Fei, Xu, Yong-Chun, Luo
Format Journal Article
LanguageEnglish
Published London Royal Society of Chemistry 18.05.2021
Subjects
Carbohydrates
Chemical reactions
Crystallography
D-Galactose
D-Ribose
Galactose
Organic chemistry
Polycyclic compounds
Proline
Ribose
Stereochemistry
Uridine
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo00228g