title: A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine.
abstract: Enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a novel chiral oxazolidine organocatalyst afforded chiral isoquinuclidines that is an efficient synthetic intermediate of oseltamivir, with fairly good chemical yield and excellent enantioselectivity (90%, up to >99% ee).
authors.affiliation: Division of Applied Science and Engineering, College of Environmental Technology, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto, Muroran, Hokkaido 050-8585, Japan. catanaka@mmm.muroran-it.ac.jp
authors.forename: Hiroto
authors.initials: H
authors.lastname: Nakano
authors.forename: Kenichi
authors.initials: K
authors.lastname: Osone
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Takeshita
authors.forename: Eunsang
authors.initials: E
authors.lastname: Kwon
authors.forename: Chigusa
authors.initials: C
authors.lastname: Seki
authors.forename: Haruo
authors.initials: H
authors.lastname: Matsuyama
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Takano
authors.forename: Yoshihito
authors.initials: Y
authors.lastname: Kohari
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry*; D002384:Catalysis; D004095:Dihydropyridines / Q000737:chemistry*; D053139:Oseltamivir / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D011812:Quinuclidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000998:Antiviral Agents; D004095:Dihydropyridines; D010080:Oxazoles; D011812:Quinuclidines; C064210:oxazolidine; D053139:Oseltamivir