title: Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling.
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.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors.forename: Valentín
authors.initials: V
authors.lastname: Hornillos
authors.forename: Anthoni W
authors.initials: AW
authors.lastname: van Zijl
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000478:Alkylation; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D001965:Bromides; D011804:Quinolines; D003300:Copper; C542964:1,2,3,4-tetrahydroquinoline