Use of a boroxazolidone complex of 3-iodo-L-tyrosine for palladium-catalyzed cross-coupling.
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.
Walker
William H
WH
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Rokita
Steven E
SE
D000480:Alkynes / Q000032:analysis / Q000138:chemical synthesis*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D007470:Monoiodotyrosine / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry*
D000480:Alkynes; D001896:Boron Compounds; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D023303:Oxazolidinones; C060387:boroxazolidone; D014443:Tyrosine; D010165:Palladium; D007470:Monoiodotyrosine