Doubly Switchable Diastereodivergent Strategy Mediated by a Chiral Sulfoxide to Access Disubstituted Tetrahydrocyclopenta­pyranone and Hexahydrocyclopentapyranol Scaffolds via Nazarov Cyclization - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2022

Doubly Switchable Diastereodivergent Strategy Mediated by a Chiral Sulfoxide to Access Disubstituted Tetrahydrocyclopenta­pyranone and Hexahydrocyclopentapyranol Scaffolds via Nazarov Cyclization

Résumé

Activated dienones bearing a chiral sulfoxide were transformed diastereodivergently into the corresponding disubstituted 3,4,5,6-tetrahydrocyclopenta[b]pyran-7(2H)-ones. The torquoselectivity of the reaction could be switched by changing the Lewis acid used as promoter. From the four possible stereoisomers, only the two trans were observed. In a second switchable diastereodivergent step, both corresponding diastereomeric 2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-7-ols were obtained via the diastereoselective reduction of the ketone by changing the reducing agent. The Lewis acids as well as the reducing agents employed in both diastereodivergent steps were achiral, the diastereoselectivities being dictated by the sulfinyl auxiliary.
Fichier non déposé

Dates et versions

hal-04637171 , version 1 (05-07-2024)

Identifiants

Citer

Erwann Grenet, Arie van Der Lee, Xavier J Salom-Roig. Doubly Switchable Diastereodivergent Strategy Mediated by a Chiral Sulfoxide to Access Disubstituted Tetrahydrocyclopenta­pyranone and Hexahydrocyclopentapyranol Scaffolds via Nazarov Cyclization. Synthesis: Journal of Synthetic Organic Chemistry, 2022, 55 (04), pp.580-597. ⟨10.1055/a-1983-2140⟩. ⟨hal-04637171⟩
0 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More