Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

Lucie Jarrige (1) , Danijel Glavač , Guillaume Levitre (2) , Pascal ́ Retailleau (2) , Guillaume Bernadat (3) , Luc Neuville (2) , Géraldine Masson (2)

1 ISM - Institut des Sciences Moléculaires
2 ICSN - Institut de Chimie des Substances Naturelles
3 MBCIS - Molécules bioactives, conception, isolement et synthèse

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.

Domaines: Chimie; Catalyse; Chimie organique

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⟩