Asymmetric addition of phenylacetylene to aromatic ketones catalyzed by zinc or titanium complexes with chiral hydroxysulfonamide

Chirality. 2009 Apr;21(4):473-9. doi: 10.1002/chir.20622.

Abstract

Various new chiral hydroxysulfonamide ligands (3a-3n, 4a-4d) were prepared. Compounds 3a, 3g, 3i, 3k-3n, 4a-4d could accelerate the reaction and reduce reaction time, and 3a, 3g, 3i, 3k-3n catalyzed the reaction without titanium. The results obtained were promising in terms of yields and enantiomeric excesses (3k up to 85% ee, 4a up to 83% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry
  • Acetylene / analogs & derivatives*
  • Acetylene / pharmacology
  • Alcohols / chemistry
  • Catalysis
  • Chemistry, Organic / methods
  • Ketones / metabolism*
  • Ligands
  • Models, Chemical
  • Stereoisomerism
  • Sulfonamides / chemistry*
  • Temperature
  • Time Factors
  • Titanium / chemistry*
  • Zinc / chemistry*

Substances

  • Acetophenones
  • Alcohols
  • Ketones
  • Ligands
  • Sulfonamides
  • phenylacetylene
  • Titanium
  • Zinc
  • Acetylene
  • acetophenone