Synlett 2015; 26(01): 127-132
DOI: 10.1055/s-0034-1378917
letter
© Georg Thieme Verlag Stuttgart · New York

A Facile and Mild Approach for Stereoselective Synthesis of α-Fluoro-α,β-unsaturated Esters from α-Fluoro-β-keto Esters via Deacylation

Jinlong Qian
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China   Fax: +86(25)84315030   Email: yiwenbin@mail.njust.edu.cn
,
Wenbin Yi*
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China   Fax: +86(25)84315030   Email: yiwenbin@mail.njust.edu.cn
,
Meifang Lv
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China   Fax: +86(25)84315030   Email: yiwenbin@mail.njust.edu.cn
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Chun Cai
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing, Jiangsu 210094, P. R. of China   Fax: +86(25)84315030   Email: yiwenbin@mail.njust.edu.cn
› Author Affiliations
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Publication History

Received: 02 August 2014

Accepted after revision: 09 October 2014

Publication Date:
05 November 2014 (online)


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Abstract

The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.

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