Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: A new class of practical Ligands for Rh-catalyzed asymmetric hydrogenation

被引:97
作者
Hu, XP [1 ]
Zheng, Z [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
D O I
10.1021/ol048519d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and application of a new family of air-stable, highly unsymmetrical ferrocene-based phosphine-phosphoramidites is described. The new ligands exhibit excellent enantioselectivities (over 99% ee) in the Rh-catalyzed asymmetric hydrogenation of enamides, dimethyl itaconate, and methyl (Z)-acetamidocinnamate even with high catalyst turnovers (S/C = 10 000). The binaphthyl moiety is crucial for reactivity and enantioselectivity, and its absolute configuration plays a dominant role in determining the chirality of the hydrogenation products.
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页码:3585 / 3588
页数:4
相关论文
共 35 条
[1]  
Berens U, 2000, ANGEW CHEM INT EDIT, V39, P1981, DOI 10.1002/1521-3773(20000602)39:11<1981::AID-ANIE1981>3.0.CO
[2]  
2-3
[3]   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
[4]   Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis [J].
Boaz, NW ;
Debenham, SD ;
Mackenzie, EB ;
Large, SE .
ORGANIC LETTERS, 2002, 4 (14) :2421-2424
[5]  
Brown J. M., 1999, COMPREHENSIVE ASYMME, V1
[6]  
BURK MJ, 1991, J AM CHEM SOC, V113, P8515
[7]  
Claver C, 2000, CHEM COMMUN, P961
[8]  
Franciò G, 2000, ANGEW CHEM INT EDIT, V39, P1428, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1428::AID-ANIE1428>3.0.CO
[9]  
2-K
[10]   Catechol-based phosphoramidites: A new class of chiral ligands for rhodium-catalyzed asymmetric hydrogenations [J].
Hoen, R ;
van den Berg, M ;
Bernsmann, H ;
Minnaard, AJ ;
de Vries, JG ;
Feringa, BL .
ORGANIC LETTERS, 2004, 6 (09) :1433-1436