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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.

SUBMITTER: Jarrige L

PROVIDER: S-EPMC6461124 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines.

Jarrige Lucie L Glavač Danijel D Levitre Guillaume G Retailleau Pascal P Bernadat Guillaume G Neuville Luc L Masson Géraldine G

Chemical science 20190207 13

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 derivat ...[more]

PMID: 31015920

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