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Synthesis 1992; 1992(8): 741-743
DOI: 10.1055/s-1992-26212
short paper
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A Convenient Asymmetric Synthesis of the Unnatural Amino Acid 2,6-Dimethyl-L-tyrosine

John H. Dygos* , Edward E. Yonan, Mike G. Scaros, Owen J. Goodmonson, Daniel P. Getman, Roy A. Periana, Gary R. Beck
  • *Chemical Development Dept., G. D. Searle and Co., 4901 Searle Parkway, Skokie, Illinois, 60077, USA
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Publication Date:
17 September 2002 (online)

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The title compound was prepared in high optical purity by a five-step synthesis from 3,5-dimethylphenol on a kilogram scale. The key steps were a modified palladium-catalyzed coupling of an aryl iodide with methyl 2-acetamidoacrylate and hydrogenation of the resulting sterically hindered dehydroamino acid 4 using [Rh(1,5-COD)- (R,R-DIPAMP)]BF4 as catalyst.