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
