Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2022

Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines

Résumé

An enantioselective chiral phosphoric acid catalyzed formal [4+2] cycloaddition between 2-benzothiazolimines and N-H-1,3-dienecarbamates is described. A divergence in reaction pathways was observed depending on the dienes employed. The reaction performed with 4-substituted dienes produced benzothiazolopyrimidines as major product in yields ranging from 42 to 67%, as single diastereoisomer and with enantioselectivity between 93 and 99%. The same reaction performed with 3-substituted dienes, however, gave highly enantioenriched 1,2,3,4-tetrahydroquinolines as the major products albeit with moderate diastereoselectivity.
Fichier principal
Vignette du fichier
hal-03660600.pdf (983.48 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-03660600 , version 1 (08-06-2022)

Licence

Paternité

Identifiants

Citer

Wei‐yang Ma, Emeric Montinho‐inacio, Bogdan Iorga, Pascal Retailleau, Xavier Moreau, et al.. Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines. Advanced Synthesis and Catalysis, 2022, 364 (10), pp.1708-1715. ⟨10.1002/adsc.202200161⟩. ⟨hal-03660600⟩

Relations

128 Consultations
41 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More