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Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives

Abstract

An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20:1 d.r.), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.

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Article information


Accepted
11 Feb 2020
First published
11 Feb 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives

Q. Ni, X. Wang, F. Xu, X. Y. Chen and X. Song, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/D0CC00736F

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