Adventures in the Chemistry of 1,1-Diacylcyclopropanes

Dedicated to Professor Armin de Meijere

Abstract

The present personalized account aims to highlight 1,1-diacylcyclopropanes as synthetic building blocks or target molecules. The chemistry presented includes cyclization reactions of 1,1-diacylcyclopropanes with free and masked dianions to give spirocyclopropanes as products or reactive intermediates that readily undergo ring-cleavage reactions. In addition, the synthesis of cyclopropylated 1,3,5-tricarbonyl compounds, containing two 1,1-diacylcyclopropane moieties, is discussed. Based on this work also other syntheses of cyclopropanes were developed.

1 Introduction

2 Reactions of Masked Dianions

3 Reactions of Free Dianions

4 Cyclopropylated 1,3,5-Tricarbonyl Compounds

5 Miscellaneous

6 Conclusions

Keywords

cyclopropanes - cyclizations - dianions - regioselectivity - silyl enol ethers

Publication History

Received: 10 February 2023

Accepted: 20 February 2023

Article published online:
21 March 2023

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