Use of a boroxazolidone complex of 3-iodo-L-tyrosine for palladium-catalyzed cross-coupling

J Org Chem. 2003 Feb 21;68(4):1563-6. doi: 10.1021/jo0207022.

Abstract

Complexation of 3-iodo-L-tyrosine with 9-borabicyclo[3.3.1]nonane (9-BBN) provides a convenient substrate for a palladium-catalyzed coupling reaction. The complex is stable to silica gel chromatography (hexanes/ethyl acetate), dilute triethylamine in THF, and potassium fluoride in DMF. The desired product, 3-ethynyl-L-tyrosine, was released from the complex by simply diluting its solution in methanol with chloroform. Interestingly, the complex remains stable in solutions of either methanol or chloroform individually.

MeSH terms

  • Alkynes / analysis
  • Alkynes / chemical synthesis*
  • Boron Compounds / chemistry*
  • Catalysis
  • Hydrocarbons, Iodinated / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Monoiodotyrosine / chemistry*
  • Oxazolidinones / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry*

Substances

  • Alkynes
  • Boron Compounds
  • Hydrocarbons, Iodinated
  • Indicators and Reagents
  • Oxazolidinones
  • boroxazolidone
  • Tyrosine
  • Palladium
  • Monoiodotyrosine