A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine | Zendy

Hiroto Nakano | Zendy; Kenichi Osone | Zendy; Mitsuhiro Takeshita | Zendy; Eunsang Kwon | Zendy; Chigusa Seki | Zendy; Haruo Matsuyama | Zendy; Nobuhiro Takano | Zendy; Yoshihito Kohari | Zendy

Open Access

A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine

Author(s) -

Hiroto Nakano,

Kenichi Osone,

Mitsuhiro Takeshita,

Eunsang Kwon,

Chigusa Seki,

Haruo Matsuyama,

Nobuhiro Takano,

Yoshihito Kohari

Publication year - 2010

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c0cc00110d

Subject(s) - enantioselective synthesis , oxazolidine , chemistry , yield (engineering) , dihydropyridine , diels–alder reaction , organic chemistry , cinchona , organocatalysis , catalysis , combinatorial chemistry , materials science , metallurgy , calcium

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).

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