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Synthesis and evaluation of a broad range of new chiral phosphine–carbene ligands for asymmetric hydrogenation
Authors:Johan Passays   Tahar Ayad   Virginie Ratovelomanana-Vidal   Annie-Claude Gaumont   Philippe Jubault  Eric Leclerc  
Affiliation:a INSA de Rouen et Université de Rouen, UMR CNRS 6014 C.O.B.R.A & FR 3038, IRCOF, 1 rue Tesnière, 76821 Mont-Saint-Aignan cedex, France;b Laboratoire Charles Friedel, UMR CNRS 7223, Ecole Nationale Supérieure de Chimie de Paris, Chimie Paristech, 11 rue Pierre et Marie Curie, 75231 Paris cedex 05, France;c Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen, 14050 Caen, France
Abstract:A straightforward and gram scale synthesis (six-step synthesis from enantioenriched β-hydroxy esters) of new structurally simple phosphine-carbene ligands bearing a single stereogenic centre has been achieved. Enantioselectivities of up to 60-63% could be achieved in the hydrogenation of methylstilbene and dehydroaminoacids when the reactions were performed under 20-50 bar hydrogen pressure.
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