Issue 30, 2012
From the journal:

Chemical Communications

Partially saturated fluorinated heterocycles: diastereo- and enantioselective synthesis of β-trifluoromethyl-pyrroline carboxylates†‡

Hiroyuki Kawai,a   Yutaka Sugita,a   Etsuko Tokunaga,a   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 Matsubara-cho, Tokyo 196-8666, Akishima, Japan

Abstract

The first asymmetric synthesis of β-trifluoromethylated pyrroline carboxylates has been achieved by organocatalytic conjugated addition of adamantyl glycine imine to β-trifluoromethylated enones, followed by a deprotection/cyclization/dehydration sequence.

Graphical abstract: Partially saturated fluorinated heterocycles: diastereo- and enantioselective synthesis of β-trifluoromethyl-pyrroline carboxylates

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Article information

DOI
https://doi.org/10.1039/C2CC18052A
Article type
Communication
Submitted
23 Dec 2011
Accepted
15 Feb 2012
First published
15 Feb 2012

Chem. Commun., 2012,48, 3632-3634

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Partially saturated fluorinated heterocycles: diastereo- and enantioselective synthesis of β-trifluoromethyl-pyrroline carboxylates

H. Kawai, Y. Sugita, E. Tokunaga, H. Sato, M. Shiro and N. Shibata, Chem. Commun., 2012, 48, 3632 DOI: 10.1039/C2CC18052A

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