D-(R)-酪氨酸的不对称催化氢化合成及其在药物合成中的应用

doi:10.6023/cjoc201305051

摘要/Abstract

以最近开发的双膦-铑配合物[Rh((R,R)-QuinoxP*)(cod)]SbF₆作为催化剂, 利用不对称催化氢化方法合成了一系列D-(R)-酪氨酸衍生物, 在S/C=10000条件下获得了99% ee的对映选择性. 并将所得的氢化产物成功应用于具有重要生理活性的化合物(R)-2-羟基-3-(3,4-二羟基苯基)丙酸钠的合成. 相比于已报道的方法, 该工艺路线产率更高而且不需要柱层析分离, 因而非常具有工业化应用前景.

关键词: 不对称催化氢化, D-(R)-酪氨酸, 铑, 双膦配体, (R)-2-羟基-3-(3,4-二羟基苯基)丙酸钠

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

引用此文

余坤矫, 张振锋, 霍小红, 王兴广, 刘德龙, 张万斌. D-(R)-酪氨酸的不对称催化氢化合成及其在药物合成中的应用[J]. 有机化学, 2013, 33(9): 1932-1938.

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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