Issue 12, 2016
From the journal:

Organic Chemistry Frontiers

3,3-Dibromo-2-trifluoromethyl acrylic acid ethyl ester: a versatile platform for the stereoselective preparation of functionalized-α-trifluoromethyl α,β-unsaturated lactones and trifluoromethyl pyrazolinones †

Satoshi Mizuta,*a   Hiroki Otaki,a   Kanami Kitamura,a   Kodai Nishi,b   Ken Watanabe,a   Juliann Nzembi Makau,a   Ryo Hashimoto,c   Toshiya Usuic  and  Kenya Chibac  

* Corresponding authors

a Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo, Nagasaki, Japan

b Department of Radioisotope Medicine, Atomic Bomb Disease institute, Nagasaki University, 1-12-4 Sakamoto, Nagasaki, Japan

c Nishiisahaya Hospital, 3015 Kaizu, Isahaya, Nagasaki 854-0063, Japan
E-mail: s-mizuta@nagasaki-u.ac.jp
Fax: +81 95 819 2864
Tel: +81 95 819 2863

Abstract

We herein describe a method for synthetic routes to multi-functionalized-α-trifluoromethyl α,β-unsaturated lactones and trifluoromethyl pyrazolinones. This involves a tandem stereoselective functionalization of 3,3-dibromo-2-trifluoromethyl acrylic acid ethyl ester and intramolecular cyclization reaction to afford precursors for a Suzuki–Miyaura cross-coupling reaction with arylboronic acids.

Graphical abstract: 3,3-Dibromo-2-trifluoromethyl acrylic acid ethyl ester: a versatile platform for the stereoselective preparation of functionalized-α-trifluoromethyl α,β-unsaturated lactones and trifluoromethyl pyrazolinones

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Article information

DOI
https://doi.org/10.1039/C6QO00360E
Article type
Research Article
Submitted
14 Jul 2016
Accepted
14 Sep 2016
First published
27 Sep 2016

Org. Chem. Front., 2016,3, 1661-1667

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3,3-Dibromo-2-trifluoromethyl acrylic acid ethyl ester: a versatile platform for the stereoselective preparation of functionalized-α-trifluoromethyl α,β-unsaturated lactones and trifluoromethyl pyrazolinones

S. Mizuta, H. Otaki, K. Kitamura, K. Nishi, K. Watanabe, J. N. Makau, R. Hashimoto, T. Usui and K. Chiba, Org. Chem. Front., 2016, 3, 1661 DOI: 10.1039/C6QO00360E

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