Issue 34, 2012
From the journal:

Chemical Communications

Catalytic enantioselective synthesis of β-trifluoromethyl pyrrolines†‡

Hiroyuki Kawai,a   Takashi Kitayama,a   Etsuko Tokunaga,a   Takashi Matsumoto,b   Hiroyasu Sato,b   Motoo Shirob  and  Norio Shibata*a  

* Corresponding authors

a Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp
Fax: +81-52-735-5442

b Rigaku Corporation, 3-9-12 Mastubara-cho, Akishima, Tokyo 196-8666, Japan

Abstract

Enantioselective synthesis of β-trifluoromethylated pyrrolines has been developed by the organocatalyzed-conjugated addition of nitromethane to β-trifluoromethylated enones, followed by a nitro-reduction/cyclization/dehydration sequence in a one-pot procedure with 97–98% ees.

Graphical abstract: Catalytic enantioselective synthesis of β-trifluoromethyl pyrrolines

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Article information

DOI
https://doi.org/10.1039/C2CC18049A
Article type
Communication
Submitted
23 Dec 2011
Accepted
09 Feb 2012
First published
10 Feb 2012

Chem. Commun., 2012,48, 4067-4069

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Catalytic enantioselective synthesis of β-trifluoromethyl pyrrolines

H. Kawai, T. Kitayama, E. Tokunaga, T. Matsumoto, H. Sato, M. Shiro and N. Shibata, Chem. Commun., 2012, 48, 4067 DOI: 10.1039/C2CC18049A

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