Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2016

Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization

Résumé

A novel aza-Prins cyclization promoted by a synergistic combination between a Lewis acid and a Brønsted acid to efficiently afford piperidines is described. Contrary to what has been previously reported in the literature, the generality of the reaction employing N-alkyl, N-aryl, and nonprotected homoallylamines has been demonstrated. The reaction is highly diastereoselective depending on the homoallylic amine used, N-PMP homoallyl amine leading preferentially to the trans diastereomer, and free homoallylamine affording the deprotected piperidine as single cis diastereomer

Domaines

Chimie
Fichier principal
Vignette du fichier
Draft JOrgChem.pdf (295.43 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-01256843 , version 1 (25-11-2020)

Identifiants

Citer

Vianney Durel, Claudia Lalli, Thierry Roisnel, Pierre van de Weghe. Synergistic Effect of the TiCl4/p-TsOH Promoter System on the Aza-Prins Cyclization. Journal of Organic Chemistry, 2016, 81 (3), pp.849-859. ⟨10.1021/acs.joc.5b02342⟩. ⟨hal-01256843⟩
85 Consultations
238 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More