Conjugate Additions to Vinyl-Substituted Aromatic N-Heterocycles

Douglas A. Klumpp

doi:10.1055/s-0031-1290984

Synlett, Table of Contents

Synlett 2012; 23(11): 1590-1604
DOI: 10.1055/s-0031-1290984

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Conjugate Additions to Vinyl-Substituted Aromatic N-Heterocycles

Douglas A. Klumpp*

Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, USA, Fax: +1(815)7534802 Email: dklumpp@niu.edu

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Abstract

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Dedicated to Professor Walter S. Trahanovksy on the occasion of his 70th birthday

Abstract

Conjugate or Michael addition to vinyl-substituted aromatic N-heterocycles has been a useful synthetic method for the synthesis of functionalized heterocyclic compounds. A wide variety of heterocycles and nucleophiles undergo this chemistry. Recent work in this area has utilized transition-metal catalysts and some asymmetric synthesis has been accomplished. An overview of this chemistry is presented in this account.

1 Introduction

2 General Aspects

3 Carbon-Centered Nucleophiles

4 Nitrogen-Centered Nucleophile

5 Oxygen and Sulfur Nucleophiles

6 Transition-Metal-Catalyzed Reactions

7 Asymmetric Conjugate Addition

8 Summary and Outlook

Key words

Michael addition - heterocycles - catalysis - nucleophilic addition - transition metals

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References

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