Issue 26, 2010
From the journal:

Chemical Communications

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

Hiroto Nakano,*a   Kenichi Osone,b   Mitsuhiro Takeshita,*b   Eunsang Kwon,c   Chigusa Seki,a   Haruo Matsuyama,a   Nobuhiro Takanoa  and  Yoshihito Koharia  

* Corresponding authors

a Division of Applied Science and Engineering, College of Environmental Technology, Guraduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto, Muroran, Hokkaido 050-8585, Japan
E-mail: catanaka@mmm.muroran-it.ac.jp
Fax: +81 14 346 5727
Tel: +81 14 346 5727

b Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan
E-mail: catanaka@tohoku-pharm.ac.jp
Fax: +81 22 727 0146
Tel: +81 22 727 0147

c Research and Analytical Center for Giant Molecules, Graduate School of Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, sendai 980-8578, Japan
E-mail: ekwon@m.tains.tohoku.ac.jp
Fax: +81 22 795 6752
Tel: +81 22 795 6752

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).

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

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Article information

DOI
https://doi.org/10.1039/C0CC00110D
Article type
Communication
Submitted
24 Feb 2010
Accepted
30 Apr 2010
First published
26 May 2010

Chem. Commun., 2010,46, 4827-4829

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

H. Nakano, K. Osone, M. Takeshita, E. Kwon, C. Seki, H. Matsuyama, N. Takano and Y. Kohari, Chem. Commun., 2010, 46, 4827 DOI: 10.1039/C0CC00110D

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