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Issue 13, 2019
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Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

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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

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Publication details

The article was received on 14 Dec 2018, accepted on 06 Feb 2019 and first published on 07 Feb 2019


Article type: Edge Article
DOI: 10.1039/C8SC05581E
Chem. Sci., 2019,10, 3765-3769
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    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

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