Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands

被引:126
作者
Axtell, AT
Cobley, CJ
Klosin, J
Whiteker, GT
Zanotti-Gerosa, A
Abboud, KA
机构
[1] Chirotech Tech Ltd, Dowpharma, Cambridge CB4 0WG, England
[2] Dow Chem Co USA, Chem Sci, S Charleston, WV 25303 USA
[3] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
[4] Dow Chem Co USA, Chem Sci, Midland, MI 48674 USA
关键词
asymmetric catalysis; hydroformylation; P ligands; rhodium;
D O I
10.1002/anie.200501478
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Off the shelf: The commercially available ligand (R,R)-1,2-bis(2,5-diphenylphospholano)ethane ((R,R)-Ph-bpe) has been identified as an excellent ligand for asymmetric hydroformylation. State-of-the-art regio- and enantioselectivities are obtained for reactions with styrene, allyl cyanide, and vinyl acetate as substrates while high reaction rates (> 4000 turnovers h-1) are maintained (see scheme; Ac = acetate, b/l = branched/linear). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5834 / 5838
页数:5
相关论文
共 28 条
[1]  
Babin J. E., 1993, World Patent, Patent No. [WO 9303839, 9303839]
[2]  
Berens U, 2000, ANGEW CHEM INT EDIT, V39, P1981, DOI 10.1002/1521-3773(20000602)39:11<1981::AID-ANIE1981>3.0.CO
[3]  
2-3
[4]  
BERENS U, 2000, ANGEW CHEM, V112, P2057
[5]  
Breeden S, 2000, ANGEW CHEM INT EDIT, V39, P4106, DOI 10.1002/1521-3773(20001117)39:22<4106::AID-ANIE4106>3.0.CO
[6]  
2-L
[7]  
BREEDEN S, 2000, ANGEW CHEM, V112, P4272
[8]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[9]   Modular phospholane ligands in asymmetric catalysis [J].
Burk, MJ .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :363-372
[10]   Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by bis-3,4-diazaphospholanes [J].
Clark, TP ;
Landis, CR ;
Freed, SL ;
Klosin, J ;
Abboud, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (14) :5040-5042