title: Enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using β-amino alcohol organocatalyst.
abstract: The enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active β-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.
authors.affiliation: Department of Bioengineering, Graduate School of Engineering, Muroran Institute of Technology , 27-1 Mizumoto, Muroran 050-8585, Japan.
authors.forename: Yoshihito
authors.initials: Y
authors.lastname: Kohari
authors.forename: Yuko
authors.initials: Y
authors.lastname: Okuyama
authors.forename: Eunsang
authors.initials: E
authors.lastname: Kwon
authors.forename: Taniyuki
authors.initials: T
authors.lastname: Furuyama
authors.forename: Nagao
authors.initials: N
authors.lastname: Kobayashi
authors.forename: Teppei
authors.initials: T
authors.lastname: Otuki
authors.forename: Jun
authors.initials: J
authors.lastname: Kumagai
authors.forename: Chigusa
authors.initials: C
authors.lastname: Seki
authors.forename: Koji
authors.initials: K
authors.lastname: Uwai
authors.forename: Gang
authors.initials: G
authors.lastname: Dai
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Iwasa
authors.forename: Hiroto
authors.initials: H
authors.lastname: Nakano
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D004095:Dihydropyridines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011812:Quinuclidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D004095:Dihydropyridines; D010880:Piperidines; D011812:Quinuclidines