Article Dans Une Revue Journal of the American Chemical Society Année : 2021

Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition

Résumé

A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.

Fichier principal
Vignette du fichier
Enantioselective and Diastereo-divergent Synthesis of Spiro-indolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition.pdf (698 Ko) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)
Licence

Dates et versions

hal-03402302 , version 1 (25-10-2021)

Licence

Identifiants

Citer

Thomas Varlet, Mateja Matišić, Elsa van Elslande, Luc Neuville, Vincent Gandon, et al.. Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition. Journal of the American Chemical Society, 2021, 143 (30), pp.11611-11619. ⟨10.1021/jacs.1c04648⟩. ⟨hal-03402302⟩
272 Consultations
652 Téléchargements

Altmetric

Partager

  • More