Issue 13, 2019

Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

Abstract

A highly efficient catalytic enantioselective [4+2] cycloaddition was developed between 2-benzothiazolimines and enecarbamates. A wide range of benzothiazolopyrimidines bearing three contiguous stereogenic centers was obtained in high to excellent yields and with excellent diastereo- and enantioselectivities (d.r. > 98 : 2 and up to >99% ee). Furthermore, this chiral phosphoric acid-catalyzed strategy was scalable and enabled access to a new class of optically pure Lewis base isothiourea derivatives.

Graphical abstract: Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

Supplementary files

Article information

Article type
Edge Article
Submitted
14 dec 2018
Accepted
06 feb 2019
First published
07 feb 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 3765-3769

Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

L. Jarrige, D. Glavač, G. Levitre, P. Retailleau, G. Bernadat, L. Neuville and G. Masson, Chem. Sci., 2019, 10, 3765 DOI: 10.1039/C8SC05581E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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