When Alkyne π-Activation Meets Pinacol-Type [1,2]-Rearrangement: On the Invention of Domino Reactions for the Synthesis of Carbocycles and Heterocycles

Klaus-Daniel Umland; Stefan F. Kirsch

doi:10.1055/s-0033-1338840

Synlett, Table of Contents

Synlett 2013; 24(12): 1471-1484
DOI: 10.1055/s-0033-1338840

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When Alkyne π-Activation Meets Pinacol-Type [1,2]-Rearrangement: On the Invention of Domino Reactions for the Synthesis of Carbocycles and Heterocycles

Klaus-Daniel Umland

Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany Fax: +49(202)4392648 Email: sfkirsch@uni-wuppertal.de

,

Stefan F. Kirsch*

Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany Fax: +49(202)4392648 Email: sfkirsch@uni-wuppertal.de

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Abstract

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Dedicated to Prof. Dr. Dr. h.c. Lutz F. Tietze, the inventor of ‘domino reactions’.

Abstract

This is a personal account on how to create domino reactions consisting of catalyzed or uncatalyzed alkyne activation, cyclization, and subsequent rearrangement by a [1,2]-shift. In the context of literature reports on breakthrough works, we discuss our motivation, challenges, and success stories. The title reactions were developed with the goal of rapidly evolving molecular complexity in an experimentally easy manner. The value of the reactions in controlled syntheses of various carbocyclic and heterocyclic scaffolds through changing the nature of the substrate and the exact reaction conditions is demonstrated.

1 Introduction

2 Carbocyclizations

2.1 6-Endo Cyclization

2.2 6-Exo Cyclization

3 Heterocyclizations

4 Miscellaneous Reactions

5 Conclusions

Key words

domino reactions - rearrangements - catalysis - heterocycles - carbocycles

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References

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