Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

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 enantiosele...

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Detalles Bibliográficos
Autores principales: Jarrige, Lucie, Glavač, Danijel, Levitre, Guillaume, Retailleau, Pascal, Bernadat, Guillaume, Neuville, Luc, Masson, Géraldine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6461124/
https://www.ncbi.nlm.nih.gov/pubmed/31015920
http://dx.doi.org/10.1039/c8sc05581e
Descripción
Sumario: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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