Issue 20, 2022

Ring contraction in synthesis of functionalized carbocycles


Carbocycles are a key and widely present structural motif in organic compounds. The construction of structurally intriguing carbocycles, such as highly-strained fused rings, spirocycles or highly-functionalized carbocycles with congested stereocenters, remains challenging in organic chemistry. Cyclopropanes, cyclobutanes and cyclopentanes within such carbocycles can be synthesized through ring contraction. These ring contractions involve re-arrangement of and/or small molecule extrusion from a parental ring, which is either a carbocycle or a heterocycle of larger size. This review provides an overview of synthetic methods for ring contractions to form cyclopropanes, cyclobutanes and cyclopentanes en route to structurally intriguing carbocycles.

Graphical abstract: Ring contraction in synthesis of functionalized carbocycles

Article information

Article type
Review Article
23 Jan 2022
First published
29 Sep 2022
This article is Open Access
Creative Commons BY license

Chem. Soc. Rev., 2022,51, 8652-8675

Ring contraction in synthesis of functionalized carbocycles

C. Hui, L. Craggs and A. P. Antonchick, Chem. Soc. Rev., 2022, 51, 8652 DOI: 10.1039/D1CS01080H

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