Asymmetric hydrogenation of alkenes lacking coordinating groups

被引:169
作者
Woodmansee, David H. [1 ]
Pfaltz, Andreas [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
关键词
CATALYZED ENANTIOSELECTIVE HYDROGENATION; TRISUBSTITUTED OLEFINS; IRIDIUM CATALYSTS; LIGANDS; COMPLEXES; ROUTE;
D O I
10.1039/c1cc11430a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric hydrogenation of olefins is one of the most important reactions for the synthesis of optically active compounds, especially in industry. Chiral iridium catalysts based on P,N ligands have strongly expanded their application range. In contrast to rhodium and ruthenium diphosphine complexes they do not require the presence of a coordinating group near the C=C bond and, therefore, allow highly enantioselective hydrogenations of largely unfunctionalized alkenes.
引用
收藏
页码:7912 / 7916
页数:5
相关论文
共 55 条
[1]   Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins [J].
Bell, S ;
Wüstenberg, B ;
Kaiser, S ;
Menges, F ;
Netscher, T ;
Pfaltz, A .
SCIENCE, 2006, 311 (5761) :642-644
[2]  
Blackmond DG, 2000, CHIRALITY, V12, P442, DOI 10.1002/(SICI)1520-636X(2000)12:5/6<442::AID-CHIR25>3.0.CO
[3]  
2-F
[4]  
Blankenstein J, 2001, ANGEW CHEM INT EDIT, V40, P4445, DOI 10.1002/1521-3773(20011203)40:23<4445::AID-ANIE4445>3.0.CO
[5]  
2-V
[6]   New mechanistic insights into the iridium- phosphanooxazoline-catalyzed hydrogenation of unfunctionalized olefins: A DFT and kinetic study [J].
Brandt, P ;
Hedberg, C ;
Andersson, PG .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :339-347
[7]   ASYMMETRIC HYDROGENATION OF UNFUNCTIONALIZED TRISUBSTITUTED OLEFINS WITH A CHIRAL TITANOCENE CATALYST [J].
BROENE, RD ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12569-12570
[8]   Iridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents [J].
Church, Tamara L. ;
Andersson, Pher G. .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :513-531
[9]   Enantioselectivity in the Iridium-Catalyzed Hydrogenation of Unfunctionalized Olefins [J].
Church, Tamara L. ;
Rasmussen, Torben ;
Andersson, Pher G. .
ORGANOMETALLICS, 2010, 29 (24) :6769-6781
[10]   CHIRAL ORGANOLANTHANIDE COMPLEXES FOR ENANTIOSELECTIVE OLEFIN HYDROGENATION [J].
CONTICELLO, VP ;
BRARD, L ;
GIARDELLO, MA ;
TSUJI, Y ;
SABAT, M ;
STERN, CL ;
MARKS, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2761-2762