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Base‐Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration
Author(s) -
Zhao Yulei,
Zhang Fangfang,
Yao Wenjun,
Wang Chengyu,
Liu Yuanyuan,
Li Yanzhong
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501060
Subject(s) - enamine , chemistry , conjugated system , nucleophile , combinatorial chemistry , diene , intermolecular force , base (topology) , organic chemistry , stereochemistry , molecule , catalysis , polymer , natural rubber , mathematical analysis , mathematics
An efficient and chemoselective nitrogen nucleophilic addition/enamine migration cascade reaction was explored, in which a range of enaminones and propynyl carbonyl compounds were converted into highly functionalized conjugated diene derivatives in good to high yields. The mechanism of the intermolecular enamine migration pathway was proposed according to the results of a cross reaction. This method provides a new and direct approach for the synthesis of conjugated diene motifs.