Synthesis of a New Bipyridyl Diphosphine Ligand and Its Application to Asymmetric Hydrogenation of β-Keto Esters

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1724-1728. Previous Articles Next Articles

Original Articles

新型联吡啶双膦配体的合成及其在β-酮酸酯不对称加氢反应中的应用

陈丽^a; 马梦林^b; 彭宗海^a; 陈华^*,a

(a四川大学化学学院有机金属络合催化研究所绿色化学与技术教育部重点实验室成都 610064)
(b西华大学化学系成都 611930)

收稿日期:2007-07-13 修回日期:2008-03-20 发布日期:2008-10-20
通讯作者: 陈华

Synthesis of a New Bipyridyl Diphosphine Ligand and Its Application to Asymmetric Hydrogenation of β-Keto Esters

CHEN, Li^a ; MA, Meng-Lin^{b ;} PENG, Zong-Hai^a ; CHEN, Hua^*,a

(^aKey Laboratory of Green Chemistry & Technology, Ministry of Education, Institute of Homogeneous Catalysis,
Faculty of Chemistry, Sichuan University, Chengdu 610064)
(^bDepartment of Chemistry, Xihua University Chengdu 611930)

Received:2007-07-13 Revised:2008-03-20 Published:2008-10-20
Contact: CHEN, Hua

Abstract

A new electron-donating diphosphine (R)-MeO-P-Phos [(R)-2,2’,6,6’-tetramethoxy-4,4’- bis[di(4-meth- oxylphenyl)phosphino]-3,3’-bipyridine] has been synthesized and its application to the asymmetric hydrogenation of β-keto esters catalyzed by ruthenium complex was explored. Solvent effect was tested and up to 99.1% ee was achieved for the hydrogenation of ethyl acetoacetate in EtOH. The asymmetric hydrogenation of various β-keto esters catalyzed by Ru-MeO-P-Phos was investigated.

Key words: β-keto ester, asymmetric hydrogenation, chiral diphosphine, enantioselectivity

Cite this article

CHEN, Li^a ; MA, Meng-Lin^{b ;} PENG, Zong-Hai^a ; CHEN, Hua^*,a. Synthesis of a New Bipyridyl Diphosphine Ligand and Its Application to Asymmetric Hydrogenation of β-Keto Esters[J]. Chin. J. Org. Chem., 2008, 28(10): 1724-1728.

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新型联吡啶双膦配体的合成及其在β-酮酸酯不对称加氢反应中的应用

Synthesis of a New Bipyridyl Diphosphine Ligand and Its Application to Asymmetric Hydrogenation of β-Keto Esters

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