Synthesis 2016; 48(16): 2637-2644
DOI: 10.1055/s-0035-1561442
special topic
© Georg Thieme Verlag Stuttgart · New York

Chiral C 2-Symmetric Iodoarene-Catalyzed Asymmetric α-Oxidation of β-Keto Esters

Yangyang Feng
a  School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, P. R. of China
b  State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. of China   Email: xiong@cqu.edu.cn
,
Ruofeng Huang
a  School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, P. R. of China
b  State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. of China   Email: xiong@cqu.edu.cn
,
Liangzhen Hu
a  School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, P. R. of China
b  State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. of China   Email: xiong@cqu.edu.cn
,
Yan Xiong*
a  School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, P. R. of China
b  State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. of China   Email: xiong@cqu.edu.cn
,
Vincent Coeffard*
c  Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines, 45 Avenue des États-Unis, 78035 Versailles cedex, France   Email: vincent.coeffard@uvsq.fr
› Author Affiliations
Further Information

Publication History

Received: 24 February 2016

Accepted after revision: 21 March 2016

Publication Date:
11 May 2016 (eFirst)

Abstract

The catalytic asymmetric oxidation of α-substituted β-keto esters promoted by C 2-symmetric iodoarenes as chiral agents and MCPBA­ as the oxidant is described. By a careful screening of the reaction conditions, promising enantiomeric excesses and moderate-to-good yields were obtained for the synthesis of β-keto esters containing a stereogenic center.

Supporting Information

 
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