Acetylenic Esters in Organic Synthesis

Abstract

Activated acetylenic substrates such as acetylenic esters and alkyl propiolates are very important in organic synthesis. Due to their electron deficiency, these compounds are widely used in combinatorial and multicomponent reactions, enabling the synthesis of a large variety of novel compounds. In addition, these substrates are powerful Michael acceptors and convenient dienophiles and dipolarophiles in Diels–Alder and 1,3-dipolar cycloaddition reactions. The addition of different nucleophiles, primarily phosphorus, nitrogen or sulfur, to the triple bonds of these substrates produces key intermediates, such as Tebby and Huisgen zwitterions, which can lead to designing pathways toward the generation of spirocyclic and polycyclic compounds. This account highlights recent studies on the chemistry of acetylenic esters and their applications in organic synthesis.

1 Introduction

2 Synthesis of Acyclic and Monocyclic Compounds

3 Synthesis of Spirocyclic Compounds

4 Synthesis of Polycyclic Compounds

5 Conclusion

Key words

acetylenic esters - Huisgen intermediates - 1,3-dipolar cycloaddition - dienophiles - dipolarophiles - spirocyclic compounds - polycyclic compounds - polysubstituted monocycles

Publication History

Received: 03 March 2022

Accepted after revision: 11 March 2022

Article published online:
09 May 2022

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