Stereodivergent synthesis of enantioenriched 4-hydroxy-2-cyclopentenones

J Org Chem. 2014 Jan 3;79(1):452-8. doi: 10.1021/jo402539p. Epub 2013 Dec 20.

Abstract

Protected 4-hydroxycyclopentenones (4-HCPs) constitute an important class of intermediates in chemical synthesis. A route to this class of compound has been developed. Key steps include Noyori reduction (which establishes the stereochemistry of the product), ring-closing metathesis, and simple functional group conversions to provide a set of substituted 4-HCPs in either enantiomeric form.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cyclopentanes
  • 4-hydroxy-2-cyclopentenone