Regioselective synthesis of functionalized 3,5-diketoesters and 2,4-diketosulfones by uncatalyzed condensation of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with alpha,beta-unsaturated acid chlorides and sulfonyl chlorides

Org Biomol Chem. 2008 Sep 21;6(18):3366-70. doi: 10.1039/b810151e. Epub 2008 Jul 25.

Abstract

The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with alpha,beta-unsaturated and functionalized acid chlorides afforded a variety of 3,5-diketoesters which are not readily available by other methods. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with sulfonyl chlorides allows a direct synthesis of 2,4-diketosulfones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Butadienes / chemistry*
  • Catalysis
  • Chlorine Compounds / chemistry*
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Ketones / chemistry*
  • Methylation
  • Models, Molecular
  • Molecular Structure
  • Oxygen / chemistry
  • Stereoisomerism
  • Sulfinic Acids / chemistry*
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Acids
  • Butadienes
  • Chlorine Compounds
  • Esters
  • Ketones
  • Sulfinic Acids
  • Sulfones
  • sulfonyl chloride
  • Oxygen