Intramolecular reductive ketone-alkynoate coupling reaction promoted by (η2-propene)titanium

Org Biomol Chem. 2012 Apr 28;10(16):3253-7. doi: 10.1039/c2ob07049a. Epub 2012 Mar 12.

Abstract

Intramolecular reductive coupling of cycloalkanones tethered to alkynoates in the presence of (η(2)-propene)titanium was successfully performed to provide hydroxy-esters in a diastereoselective manner. Subsequent lactonization afforded angularly fused unsaturated tricyclic lactones which represent relevant substructures of numerous bioactive compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Cyclization
  • Esters / chemical synthesis
  • Esters / chemistry
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Oxidation-Reduction
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Alkenes
  • Esters
  • Ketones
  • Lactones
  • propylene
  • Titanium