Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling.

TitleCatalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling.
Publication TypeJournal Article
Year of Publication2012
AuthorsHornillos V, van Zijl AW, Feringa BL
JournalChemical communications (Cambridge, England)
Volume48
Issue31
Pagination3712-4
Date Published2012 Apr 18
Abstract

Highly enantioselective synthesis of chiral chromenes and tetrahydroquinolines is achieved by combining asymmetric copper-catalyzed allylic substitution with Grignard reagents and an efficient intramolecular Heck reaction. Moreover, the exocyclic double bond formed in the cyclisation was subjected to RCM, hydroboration and hydrogenation illuminating the synthetic versatility of these heterocycles.

DOI10.1007/s12975-011-0110-4
Alternate JournalChem. Commun. (Camb.)