[2+2+1] cyclization of allenes

Chem Soc Rev. 2014 May 7;43(9):2956-78. doi: 10.1039/c3cs60382b. Epub 2014 Feb 11.

Abstract

The [2+2+1] cyclization of an alkyne, an alkene and carbon monoxide, i.e., the Pauson-Khand reaction, is one of the most powerful tools for constructing a five-membered ring. In place of the alkene or alkyne part, the use of an allene functionality has proven to make this reaction more valuable for organic synthesis. This review focuses on the origin and progress of the allenic [2+2+1] cyclocarbonylation, including the chirality transfer of the allene and its synthetic applications.

Publication types

  • Review

MeSH terms

  • Alkadienes / chemical synthesis
  • Alkadienes / chemistry*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Bridged Bicyclo Compounds / chemical synthesis
  • Bridged Bicyclo Compounds / chemistry
  • Chemistry Techniques, Synthetic / methods*
  • Cyclization
  • Cyclopentanes / chemical synthesis
  • Cyclopentanes / chemistry
  • Polyenes / chemical synthesis
  • Polyenes / chemistry
  • Stereoisomerism

Substances

  • Alkadienes
  • Biological Products
  • Bridged Bicyclo Compounds
  • Cyclopentanes
  • Polyenes
  • propadiene
  • cyclopentenone