Tertiary Enamides as Versatile and Valuable Substrates to Reach Chemical Diversity

Frédéric Beltran; Laurence Miesch

doi:10.1055/s-0040-1707403

Synthesis, Table of Contents

Synthesis 2020; 52(17): 2497-2511
DOI: 10.1055/s-0040-1707403

short review

Tertiary Enamides as Versatile and Valuable Substrates to Reach Chemical Diversity

Frédéric Beltran

^aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

,

Laurence Miesch∗

^bÉquipe Synthèse Organique et Phytochimie, Institut de Chimie, CNRS-UdS UMR 7177, 4, rue Blaise Pascal CS 90032, 67081 Strasbourg, France Email: lmiesch@unistra.fr

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Abstract

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Abstract

Tertiary enamides display versatile reactivity and great stability compared to their enamine congeners. This review covers progress made in the development of new methods involving the enaminic reactivity of tertiary enamides with respect to the synthesis of complex nitrogen-containing compounds. A focus on the preparation of biologically active molecules is also presented. The syntheses reported herein are classified based on their reaction type. In addition, mechanistic insights are given for most of the new transformations.

1 Introduction

2 [2+2] Cycloadditions

3 [4+2] Cycloadditions

4 Electrocyclizations and Cycloisomerizations

5 Sigmatropic Rearrangements

6 Nucleophilic Additions

7 Tertiary Enamides as Electrophiles

8 Cross-Coupling Reactions

9 Tertiary-Enamide-Assisted Reactions

10 Conclusion and Perspectives

Key words

tertiary enamides - N-heterocycles - cycloadditions - pericyclic reactions - nucleophilic additions - cross-coupling reactions - tertiary-enamide-assisted reactions

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References

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