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

doi:10.1055/s-1992-26212

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

Abstract

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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.

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