Convenient General Asymmetric Synthesis of Roche Ester Derivatives through Catalytic Asymmetric Hydrogenation: Steric and Electronic Effects of Ligands

被引：34

作者：

Pautigny, Cyrielle ^{[1
]}

Jeulin, Severine ^{[1
]}

Ayad, Tahar ^{[1
]}

Zhang, Zhaoguo ^{[2
,3
]}

Genet, Jean-Pierre ^{[1
]}

Ratovelomanana-Vidal, Virginie ^{[1
]}

机构：

[1] Ecole Natl Super Chim Paris, CNRS, UMR 7573, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France

[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Technol, Shanghai 200240, Peoples R China

[3] Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 16期

关键词：

asymmetric catalysis; hydrogenation; Roche ester; ruthenium;

D O I：

10.1002/adsc.200800504

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient and concise asymmetric hydrogenation of acrylate esters promoted by the cationic ruthenium monohydride complex [Ru(H)(eta(6)-cot)SYNPHOS]+BF4- is reported. A full investigation of the effects of catalyst precursors, solvents, temperature, hydrogen pressure, substrates as well as steric and electronic properties of ligands was carried out. The corresponding valuable Roche ester derivatives were obtained in good to excellent isolated yields and high enantioselectivities under mild conditions. The robustness and practicability of this highly enantioselective hydrogenation was demonstrated by the synthesis of the 3-hydroxy-2-methylpropanoic acid tert-butyl ester on a multigram scale, resulting III excellent yield and ee up to 94%.

引用

页码：2525 / 2532

页数：8

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