Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins

被引:35
作者
Marson, Angelica
Freixa, Zoraida
Kamer, Paul C. J.
van Leeuwen, Piet W. N. M. [1 ]
机构
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[3] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WV Amsterdam, Netherlands
关键词
homogeneous catalysis; stereoselective catalysis; asymmetric hydrogenation; calixarenes; diphosphites;
D O I
10.1002/ejic.200700764
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral calixarene-based diphosphite ligands 3a-d have been obtained via lower-rim functionalisation of the p-tert-butylcalix[4]arene core. High enantiomeric excesses (up to 94 %) and good activities were obtained in the rhodium-catalyzed asymmetric hydrogenation of prochiral olefins with TADDOL-containing diphosphites 3c,d. This is the first example of chiral calix[4]arene-modified ligands that induce high enantioselectivity in metal-catalysed asymmetric reactions.
引用
收藏
页码:4587 / 4591
页数:5
相关论文
共 46 条
[31]   Synthesis of a calix[6]arene-derived diphosphite, its palladium and platinum complexes, and the remarkable activity of (syn-calix[6]arene diphosphite)Pd(CH3) (CH3CN)OTf in carbon monoxide and ethene copolymerization [J].
Parlevliet, FJ ;
Zuideveld, MA ;
Kiener, C ;
Kooijman, H ;
Spek, AL ;
Kamer, PCJ ;
van Leeuwen, PWNM .
ORGANOMETALLICS, 1999, 18 (17) :3394-3405
[32]   Generation of new enzymes via covalent modification of existing proteins [J].
Qi, DF ;
Tann, CM ;
Haring, D ;
Distefano, MD .
CHEMICAL REVIEWS, 2001, 101 (10) :3081-3111
[33]  
Reetz M. T., 1999, ANGEW CHEM, V111, P134
[34]   Controlling the enantioselectivity of enzymes by directed evolution: Practical and theoretical ramifications [J].
Reetz, MT .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5716-5722
[35]  
Reetz MT, 2000, ANGEW CHEM INT EDIT, V39, P3889, DOI 10.1002/1521-3773(20001103)39:21<3889::AID-ANIE3889>3.0.CO
[36]  
2-T
[37]  
Reetz MT, 1999, ANGEW CHEM INT EDIT, V38, P179
[38]   DERIVATIVES OF ALPHA,ALPHA,ALPHA',ALPHA'-TETRAARYL-2,2-DIMETHYL-1,3-DIOXOLAN-4,5-DIMETHANOL (TADDOL) CONTAINING NITROGEN, SULFUR, AND PHOSPHORUS ATOMS - NEW LIGANDS AND AUXILIARIES FOR ENANTIOSELECTIVE REACTIONS [J].
SEEBACH, D ;
HAYAKAWA, M ;
SAKAKI, J ;
SCHWEIZER, WB .
TETRAHEDRON, 1993, 49 (09) :1711-1724
[39]  
SEMERIL D, 2006, ANGEW CHEM, V118, P5942
[40]   Regioselectivity with hemispherical chelators:: Increasing the catalytic efficiency of complexes of diphosphanes with large bite angles [J].
Semeril, David ;
Jeunesse, Catherine ;
Matt, Dominique ;
Toupet, Loic .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5810-5814