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Current Organic Chemistry

Author(s): Ana L. Cardoso* and Maria I.L. Soares*

DOI: 10.2174/1385272823666191203122959

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1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings

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Abstract

The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked.

This review summarizes the most relevant research in which allenes are used as building blocks for the construction of structurally diverse five-membered rings via [3+2] annulation reactions.

Keywords: Allenes, allenoates, annulation, carbocycles, cycloaddition, dipoles, five-membered ring, heterocycles, phosphine catalysis.

Graphical Abstract

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