Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines - Archive ouverte HAL
Article Dans Une Revue Chemical Science Année : 2019

Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

Résumé

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.
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Dates et versions

hal-02324689 , version 1 (22-10-2019)

Identifiants

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Lucie Jarrige, Danijel Glavač, Guillaume Levitre, Pascal ́ Retailleau, Guillaume Bernadat, et al.. Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines. Chemical Science, 2019, 10 (13), pp.3765-3769. ⟨10.1039/c8sc05581e⟩. ⟨hal-02324689⟩
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