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 deri...

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Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 10; pp. 2203 - 2207
Main Authors Zhang, Jie-Hui, Pan, Cheng-Lin, Zhang, Huan-Huan, Xu, Peng-Fei, Luo, Yong-Chun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.05.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOSIDE
ASYMMETRIC 3+2 CYCLOADDITION
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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:2052-4129
DOI:10.1039/d1qo00228g