title: Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction.
abstract: An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
authors.forename: Laura L
authors.initials: LL
authors.lastname: Taylor
authors.forename: Frederick W
authors.initials: FW
authors.lastname: Goldberg
authors.forename: King Kuok Mimi
authors.initials: KK
authors.lastname: Hii
mesh_terms: D000478:Alkylation; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis*; D027821:Rutaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D011804:Quinolines; D010165:Palladium; C542964:1,2,3,4-tetrahydroquinoline