BINOL derived monodentate acylphosphite ligands for homogeneously catalyzed enantioselective hydrogenation

被引:26
作者
Korostylev, A
Monsees, A
Fischer, C
Borner, A
机构
[1] Univ Rostock, Leibniz Inst Organ Katal, D-18055 Rostock, Germany
[2] Degussa AG, Projekthuas Katal, Geschaftsbereich Creavis, Ind Hoechst, D-65926 Frankfurt, Germany
[3] Univ Rostock, Fachbereich Chem, D-18059 Rostock, Germany
关键词
D O I
10.1016/j.tetasy.2004.01.012
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiopure acylphosphites have been prepared based upon chiral nonsubstituted and 3,3'-disubstituted binaphthols in order to elucidate steric and electronic effects on the Rh(I)-catalyzed asymmetric hydrogenation of functionalized olefins. With these new types of ligands, up to 80% ee was obtained. Rate as well as enantio selectivity of the hydrogenation were strongly dependent on the precatalyst preparation and substitution pattern of the ligand. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1001 / 1005
页数:5
相关论文
共 33 条
[1]   Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].
Arnold, LA ;
Imbos, R ;
Mandoli, A ;
de Vries, AHM ;
Naasz, R ;
Feringa, BL .
TETRAHEDRON, 2000, 56 (18) :2865-2878
[2]   Enantioselective catalysis in fine chemicals production [J].
Blaser, HU .
CHEMICAL COMMUNICATIONS, 2003, (03) :293-296
[3]   Enantioselective catalysis in fine chemicals production [J].
Blaser, HU ;
Spindler, F ;
Studer, A .
APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) :119-143
[4]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[5]  
Brown J. M, 1999, COMPREHENSIVE ASYMME, VI, P121
[6]   Synthesis of novel chiral binaphthyl phosphorus ligands and their applications in Rh-catalyzed asymmetric hydrogenation [J].
Chi, YX ;
Zhang, XM .
TETRAHEDRON LETTERS, 2002, 43 (27) :4849-4852
[7]  
Claver C, 2000, CHEM COMMUN, P961
[8]   HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS [J].
CRAM, DJ ;
HELGESON, RC ;
PEACOCK, SC ;
KAPLAN, LJ ;
DOMEIER, LA ;
MOREAU, P ;
KOGA, K ;
MAYER, JM ;
CHAO, Y ;
SIEGEL, MG ;
HOFFMAN, DH ;
SOGAH, GDY .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1930-1946
[9]  
Franciò G, 1999, EUR J INORG CHEM, P1219
[10]   Synthesis of new chiral monodentate phosphite ligands and their use in catalytic asymmetric hydrogenation [J].
Hua, ZH ;
Vassar, VC ;
Ojima, I .
ORGANIC LETTERS, 2003, 5 (21) :3831-3834