A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine.
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).
Nakano
Hiroto
H
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
Osone
Kenichi
K
Takeshita
Mitsuhiro
M
Kwon
Eunsang
E
Seki
Chigusa
C
Matsuyama
Haruo
H
Takano
Nobuhiro
N
Kohari
Yoshihito
Y
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
D000998:Antiviral Agents; D004095:Dihydropyridines; D010080:Oxazoles; D011812:Quinuclidines; C064210:oxazolidine; D053139:Oseltamivir