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Convenient General Asymmetric Synthesis of Roche Ester Derivatives through Catalytic Asymmetric Hydrogenation: Steric and Electronic Effects of Ligands
Author(s) -
Pautigny Cyrielle,
Jeulin Séverine,
Ayad Tahar,
Zhang Zhaoguo,
Genêt JeanPierre,
RatovelomananaVidal Virginie
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800504
Subject(s) - chemistry , steric effects , enantioselective synthesis , asymmetric hydrogenation , catalysis , ruthenium , cationic polymerization , organic chemistry , yield (engineering) , acrylate , electronic effect , combinatorial chemistry , polymer , monomer , materials science , metallurgy
An efficient and concise asymmetric hydrogenation of acrylate esters promoted by the cationic ruthenium monohydride complex [Ru(H)(η 6 ‐cot)SYNPHOS] + BF 4 − 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 in excellent yield and ee up to 94%.