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

Autor:	Séverine Jeulin, Cyrielle Pautigny, Zhaoguo Zhang, Jean-Pierre Genêt, Virginie Ratovelomanana-Vidal, Tahar Ayad
Rok vydání:	2009
Předmět:	Steric effects chemistry.chemical_compound Chemistry Asymmetric hydrogenation Electronic effect Cationic polymerization Enantioselective synthesis chemistry.chemical_element General Medicine Roche ester Combinatorial chemistry Catalysis Ruthenium
Zdroj:	ChemInform. 40
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200911063
Popis:	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%.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::40311f3d8c5ed2caedd08d7d96b277ae https://doi.org/10.1002/chin.200911063 Zobrazit plný text záznamu Plný text