Dual Roles of α,β‐Unsaturated Oximes in Copper Catalyzed [3+3] Cyclization: Construction of 2,4,6‐Trisubstituted Pyridines

A new approach to generate 2,4,6‐trisubstituted pyridines was successfully developed based on the cyclization of α,β‐unsaturated oximes catalyzed by copper(I). The method takes advantage of the inherent properties of α,β‐unsaturated oximes to generate pyridines. In this transformation, α,β‐unsaturat...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2018-08, Vol.7 (8), p.1565-1570
Main Authors: Liu, Jianming, Zhao, Shufang, Yan, Xuyang, Wang, Zhixian, Zhang, Yanyan, Zhao, Peizheng, Fang, Wenhan, Zhuo, Kelei, Yue, Yuanyuan
Format: Article
Language:English
Subjects:
Copper
Copper compounds
cyclization
Michael addition
Organic chemistry
Oximes
Pyridines
trisubstituted pyridines
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Summary:A new approach to generate 2,4,6‐trisubstituted pyridines was successfully developed based on the cyclization of α,β‐unsaturated oximes catalyzed by copper(I). The method takes advantage of the inherent properties of α,β‐unsaturated oximes to generate pyridines. In this transformation, α,β‐unsaturated oximes play dual roles in the formation of nucleophilic copper(II) enamide and as the acceptor in the Michael addition. A new approach to generate 2,4,6‐trisubstituted pyridines was successfully developed based on the cyclization of α,β‐unsaturated oximes catalyzed by copper(I). The method takes advantage of the inherent properties of α,β‐unsaturated oximes to generate pyridines. In this transformation, α,β‐unsaturated oximes play dual roles in the formation of nucleophilic copper(II) enamide and as the acceptor in the Michael addition.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800318