Synthesis and evaluation of a broad range of new chiral phosphine-carbene ligands for asymmetric hydrogenation

被引:9
作者
Passays, Johan [1 ,2 ,3 ]
Ayad, Tahar [4 ]
Ratovelomanana-Vidal, Virginie [4 ]
Gaumont, Annie-Claude [5 ,6 ]
Jubault, Philippe [1 ,2 ,3 ]
Leclerc, Eric [1 ,2 ,3 ]
机构
[1] INSA Rouen, F-76821 Mont St Aignan, France
[2] Univ Rouen, CNRS, UMR 6014, COBRA, F-76821 Mont St Aignan, France
[3] Univ Rouen, FR 3038, IRCOF, F-76821 Mont St Aignan, France
[4] Chim Paristech, Lab Charles Friedel, Ecole Natl Super Chim Paris, CNRS,UMR 7223, F-75231 Paris 05, France
[5] ENSICAEN, Lab Chim Mol & Thioorgan, CNRS, UMR 6507,INC3M,FR 3038, F-14050 Caen, France
[6] Univ Caen, F-14050 Caen, France
关键词
N-HETEROCYCLIC CARBENES; SUBSTITUTED BETA-AMIDOPHOSPHINES; PALLADIUM COMPLEXES; ENANTIOSELECTIVE HYDROGENATION; OLEFIN METATHESIS; IMIDAZOLIUM SALTS; NHC LIGANDS; CATALYSTS; CHEMISTRY; HYDROSILYLATION;
D O I
10.1016/j.tetasy.2011.02.017
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A straightforward and gram scale synthesis (six-step synthesis from enantioenriched beta-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. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:562 / 574
页数:13
相关论文
共 69 条
[21]   Stability and reactivity of N-heterocyclic carbene complexes [J].
Crudden, CM ;
Allen, DP .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2247-2273
[22]   Synthesis and molecular modeling studies of SYNPHOS®, a new, efficient diphosphane ligand for ruthenium-catalyzed asymmetric hydrogenation [J].
de Paule, SD ;
Jeulin, S ;
Ratovelomanana-Vidal, V ;
Genêt, JP ;
Champion, N ;
Dellis, P .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) :1931-1941
[23]   Palladium Complexes of Planar Chiral Ferrocenyl Phosphine-NHC Ligands: New Catalysts for the Asymmetric Suzuki-Miyaura Reaction [J].
Debono, Nathalie ;
Labande, Agnes ;
Manoury, Eric ;
Daran, Jean-Claude ;
Poli, Rinaldo .
ORGANOMETALLICS, 2010, 29 (08) :1879-1882
[24]   Parallel synthesis and screening of polymer-supported phosphorus-stereogenic aminophosphane-phosphite and -phosphinite ligands [J].
den Heeten, Rene ;
Swennenhuis, Bert H. G. ;
van Leeuwen, Piet W. N. M. ;
de Vries, Johannes G. ;
Kamer, Paul C. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6602-6605
[25]  
DEPAULE SD, 2001, Patent No. 2830254
[26]  
DEPAULE SD, 2003, Patent No. 03029259
[27]   N-Heterocyclic Carbenes in Late Transition Metal Catalysis [J].
Diez-Gonzalez, Silvia ;
Marion, Nicolas ;
Nolan, Steven P. .
CHEMICAL REVIEWS, 2009, 109 (08) :3612-3676
[28]   New chiral 1,3-diphosphine ligands for Rh-catalyzed enantioselective hydrogenation:: a search for electronic effects [J].
Dubrovina, NV ;
Tararov, VI ;
Monsees, A ;
Spannenberg, A ;
Kostas, ID ;
Börner, A .
TETRAHEDRON-ASYMMETRY, 2005, 16 (22) :3640-3649
[29]  
FALDINI L, 2003, CHEM COMMUN, P30
[30]   High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview [J].
Farina, V .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1553-1582