Ring contraction in synthesis of functionalized carbocycles

Chem Soc Rev. 2022 Oct 17;51(20):8652-8675. doi: 10.1039/d1cs01080h.

Abstract

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.

Publication types

  • Review

MeSH terms

  • Cyclization
  • Cyclobutanes* / chemistry
  • Cyclopentanes / chemistry
  • Cyclopropanes / chemistry
  • Stereoisomerism

Substances

  • Cyclobutanes
  • Cyclopentanes
  • Cyclopropanes