Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

• DOI: 10.1039/c8sc05581e
• Publication Date: 2019-02-07T15:11:25Z
• Authors: Lucie Jarrige; Danijel Glavač; Guillaume Levitre; Pascal Retailleau; Guillaume Bernadat; Luc Neuville; Géraldine Masson
• Keywords: Phosphoric acid

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