Conjugate Additions to Vinyl-Substituted Aromatic N-Heterocycles

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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