Lewis Acid Induced Switch of Torquoselectivity in the Nazarov Cyclization of Activated Dienones Bearing a Chiral Sulfoxide - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2016

Lewis Acid Induced Switch of Torquoselectivity in the Nazarov Cyclization of Activated Dienones Bearing a Chiral Sulfoxide

Résumé

A Nazarov cyclization of activated dienones bearing a dihydropyran as an electron-donating group (EDG) and a chiral sulfoxide group as an electron-withdrawing group (EWG) and chiral inductor is described. The direction of the torquoselectivity depends highly on the nature of the Lewis acid promoter. This diastereodivergent strategy furnishes both trans stereoisomers from a common precursor. The potential of the Nazarov cyclization products was highlighted by further synthetic elaboration

Domaines

Chimie organique

Dates et versions

hal-03468349 , version 1 (08-12-2021)

Identifiants

Citer

Erwann Grenet, Jean Martínez, Xavier Salom-Roig. Lewis Acid Induced Switch of Torquoselectivity in the Nazarov Cyclization of Activated Dienones Bearing a Chiral Sulfoxide. Chemistry - A European Journal, 2016, 22 (47), pp.16770-16773. ⟨10.1002/chem.201603920⟩. ⟨hal-03468349⟩
10 Consultations
1 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More