Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines. Issue 13 (27th February 2019)

• Record Type: Journal Article
• Authors: Jarrige, Lucie; Glavač, Danijel; Levitre, Guillaume; Retailleau, Pascal; Bernadat, Guillaume; Neuville, Luc; Masson, Géraldine
• Is Part Of: Chemical science. Volume 10:Issue 13(2019)
• Page Start: 3765
• Page End: 3769
• Publication Date: 2019-02-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc05581e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Chiral phosphoric acid catalyzed the formal [4+2]-cycloaddition of 2-benzothiazolimines with enecarbamates to provide benzothiazolopyrimidines with up to 99% yield and >99% ee. 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.