Synthesis of D-(R)-Tyrosine by Catalytic Asymmetric Hydrogenation and Its Practical Application

doi:10.6023/cjoc201305051

Abstract

Using a recently developed catalyst[Rh((R,R)-QuinoxP*)(cod)]SbF₆, several derivatives of D-(R)-tyrosine were prepared with up to 99% ee via catalytic asymmetric hydrogenation. The substrates chosen for asymmetric hydrogenation were readily synthesized from the inexpensive and accessible compound 4-hydroxybenzaldehyde. The product resulting from the asymmetric hydrogenation was practically applied to the preparation of an important bioactive compound sodium (R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate through a feasible process.

Key words: catalytic asymmetric hydrogenation, D-(R)-tyrosine, rhodium, biphosphine ligand, sodium (R)-3-(3,4-dihydr- oxyphenyl)-2-hydroxypropanoate

Cite this article

Yu Kunjiao, Zhang Zhenfeng, Huo Xiaohong, Wang Xingguang, Liu Delong, Zhang Wanbin. Synthesis of D-(R)-Tyrosine by Catalytic Asymmetric Hydrogenation and Its Practical Application[J]. Chin. J. Org. Chem., 2013, 33(9): 1932-1938.

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