Synlett 2017; 28(16): 2163-2168
DOI: 10.1055/s-0036-1590805
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Cleavage of Unstrained C–C Bonds for the Synthesis of 1-Acyloxy-2,2,6,6-tetramethylpiperidines from Cyclic or Acyclic Ketones

Qijian Jiang
a   College of Chemical Engineering, Xiangtan University, Xiangtan 411105, P. R. of China
,
Luo Yang
c   College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. of China   eMail: wzhou@xtu.edu.cn
,
Wang Zhou  *
a   College of Chemical Engineering, Xiangtan University, Xiangtan 411105, P. R. of China
b   State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Road 38, Beijing 100191, P. R. of China
› Institutsangaben
Financial support from National Science Foundation of China (No. 21372188), Hunan Provincial Natural Science Foundation (14JJ6012), and the State Key Laboratory of Natural and Biomimetic Drugs are greatly appreciated.
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Publikationsverlauf

Received: 17. April 2017

Accepted after revision: 22. Mai 2017

Publikationsdatum:
13. Juli 2017 (online)


Abstract

A copper-catalyzed approach for the synthesis of 1-acyloxy-2,2,6,6-tetramethylpiperidines through the C–C bond cleavage of cyclic or acyclic ketones was developed. In this chemistry, a combination of CuCl2·2H2O, 1,10-phenanthroline monohydrate, and aniline was crucial for the formation of the desired products by the reaction of ketones with TEMPO. This research provides a new strategy for the further transformation of α-aryl cyclic or acyclic ketones.

Supporting Information

 
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