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Use of a Boroxazolidone Complex of 3-iodo-L-tyrosine for Palladium-Catalyzed Cross-Coupling

William H Walker 4th, Steven E Rokita

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

PMID: 12585904

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP70780 3-Iodo-L-tyrosine 3-Iodo-L-tyrosine 70-78-0 Price
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