P/S ligands derived from carbohydrates in Rh-catalyzed hydrosilylation of ketones

被引:11
作者
Khiar, Noureddine [1 ]
Pernia Leal, Manuel [1 ]
Navas, Raquel [1 ]
Francisco Moya, Juan [1 ]
Garcia Perez, Maria Victoria [2 ]
Fernandez, Inmaculada [2 ]
机构
[1] Univ Seville, CSIC, IIQ, Seville 41092, Spain
[2] Univ Seville, Fac Farm, Dept Quim Organ & Farmaceut, E-41012 Seville, Spain
关键词
ASYMMETRIC HYDROSILYLATION; ENANTIOSELECTIVE CATALYSIS; SULFINYL CHLORIDES; PHOSPHORUS LIGANDS; CARBONYL-COMPOUNDS; HYDROGENATION; COMPLEXES; RHODIUM; THIOGLYCOSIDES; TEMPERATURE;
D O I
10.1039/c1ob06305g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported is the synthesis of a number of diastereomerically pure cationic Rh(I)-complexes I starting from phosphinite thioglycosides. These complexes were used in the asymmetric hydrosilylation of prochiral ketones. The reactivity and enantioselectivity of the reaction was shown to be dependent on the pyranose ring, the substituent at the sulfur atom, the hydroxylic protective groups and most significantly on the alkene co-ligand.
引用
收藏
页码:355 / 360
页数:6
相关论文
共 54 条
[1]   THE STEREODYNAMICS OF METAL-COMPLEXES OF SULFUR-CONTAINING, SELENIUM-CONTAINING, AND TELLURIUM-CONTAINING LIGANDS [J].
ABEL, EW ;
BHARGAVA, SK ;
ORRELL, KG .
PROGRESS IN INORGANIC CHEMISTRY, 1984, 32 :1-118
[2]   NUCLEAR-MAGNETIC-RESONANCE INVESTIGATIONS OF A NOVEL INTRAMOLECULAR METHYLTHIO REPLACEMENT PROCESS IN PALLADIUM(II) AND PLATINUM(II) COMPLEXES OF MIXED SULFUR PHOSPHINE-LIGANDS [J].
ABEL, EW ;
DORMER, JC ;
ELLIS, D ;
ORRELL, KG ;
SIK, V ;
HURSTHOUSE, MB ;
MAZID, MA .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (06) :1073-1080
[3]   Putting chirality to work: The strategy of chiral switches [J].
Agranat, I ;
Caner, H ;
Caldwell, A .
NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (10) :753-768
[4]  
[Anonymous], 1999, COMPREHENSIVE ASYMME
[5]   Progress in enantioselective catalysis assessed from an industrial point of view [J].
Blaser, HU ;
Pugin, B ;
Spindler, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 231 (1-2) :1-20
[6]   Enantioselective catalysis in fine chemicals production [J].
Blaser, HU .
CHEMICAL COMMUNICATIONS, 2003, (03) :293-296
[7]   Carbohydrates as synthetic tools in organic chemistry [J].
Boysen, Mike M. K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (31) :8649-8659
[8]   C1 and C2-symmetric carbohydrate phosphorus ligands in asymmetric catalysis [J].
Castillón, S ;
Claver, C ;
Díaz, Y .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (08) :702-713
[9]   Designing the "search pathway" in the development of a new class of highly efficient stereoselective hydrosilylation catalysts [J].
César, V ;
Bellemin-Laponnaz, S ;
Wadepohl, H ;
Gade, LH .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (09) :2862-2873
[10]  
Christmann M., 2008, ASSYMMETRIC SYNTHESI