Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration

Yulei Zhao; Fangfang Zhang; Wenjun Yao; Chengyu Wang; Yuanyuan Liu; Yanzhong Li

doi:10.1002/ejoc.201501060

Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration

Yulei Zhao
, Fangfang Zhang
, Wenjun Yao
, Chengyu Wang
, Yuanyuan Liu^*
, Yanzhong Li

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	7984-7991
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	36
DOIs	https://doi.org/10.1002/ejoc.201501060
State	Published - 1 Dec 2015

Keywords

Chemoselectivity
Conjugation
Dienes
Domino reactions
Nucleophilic addition

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10.1002/ejoc.201501060

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title = "Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration",

abstract = "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.",

keywords = "Chemoselectivity, Conjugation, Dienes, Domino reactions, Nucleophilic addition",

author = "Yulei Zhao and Fangfang Zhang and Wenjun Yao and Chengyu Wang and Yuanyuan Liu and Yanzhong Li",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/ejoc.201501060",

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TY - JOUR

T1 - Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration

AU - Zhao, Yulei

AU - Zhang, Fangfang

AU - Yao, Wenjun

AU - Wang, Chengyu

AU - Liu, Yuanyuan

AU - Li, Yanzhong

PY - 2015/12/1

Y1 - 2015/12/1

N2 - 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.

AB - 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.

KW - Chemoselectivity

KW - Conjugation

KW - Dienes

KW - Domino reactions

KW - Nucleophilic addition

UR - https://www.scopus.com/pages/publications/84950103519

U2 - 10.1002/ejoc.201501060

DO - 10.1002/ejoc.201501060

M3 - 文章

AN - SCOPUS:84950103519

SN - 1434-193X

VL - 2015

SP - 7984

EP - 7991

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 36

ER -

Base-Promoted Approach to Highly Functionalized Conjugated Dienes through Enamine Migration

Abstract

Keywords

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