Axial chirality control of tropos BIPHEP-Rh complexes by chiral dienes: synergy effect in catalytic asymmetric hydrogenation

被引:29
作者
Aikawa, Kohsuke [1 ]
Takabayashi, Yuki [1 ]
Kawauchi, Susumu [2 ]
Mikami, Koichi [1 ]
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
[2] Tokyo Inst Technol, Dept Organ & Polymer Mat, Tokyo 1528552, Japan
关键词
D O I
10.1039/b809683j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diastereopure tropos Rh complexes bearing not only BIPHEP but also chiral dienes can be employed as highly enantioselective hydrogenation catalysts for an olefinic substrate.
引用
收藏
页码:5095 / 5097
页数:3
相关论文
共 41 条
[1]   Asymmetric synergy between chiral dienes and diphosphines in cationic Rh(I)-catalyzed intramolecular [4+2] cycloaddition [J].
Aikawa, Kohsuke ;
Akutagawa, Susumu ;
Mikami, Koichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12648-12649
[2]   Asymmetric catalysis with the normally unresolvable, conformationally dynamic 2,2′-bis(diphenylphosphino)-1,1′-biphenyl (biphep) [J].
Becker, JJ ;
White, PS ;
Gagné, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9478-9479
[3]  
BELLER M, 1998, TRANSITION METALS OR
[4]   Chiral olefins as steering ligands in asymmetric catalysis [J].
Defieber, Christian ;
Gruetzmacher, Hansjoerg ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502
[5]   The activation barrier to axial torsion in 2,2'-bis(diphenylphosphino)biphenyl [J].
Desponds, O ;
Schlosser, M .
TETRAHEDRON LETTERS, 1996, 37 (01) :47-48
[6]   Highly efficient asymmetric lewis acid catalysis with platinum group complexes of conformationally flexible 1,3-butadiene-bridged diphosphines, NUPHOS [J].
Doherty, S ;
Newman, CR ;
Rath, RK ;
Luo, HK ;
Nieuwenhuyzen, M ;
Knight, JG .
ORGANIC LETTERS, 2003, 5 (21) :3863-3866
[7]   Rhodium-catalyzed double [2+2+2] cycloaddition of 1, 4-bis(diphenylphosphinoyl)buta-1, 3-diyne with tethered diynes: A modular, highly versatile single-pot synthesis of NU-BIPHEP biaryl diphosphines [J].
Doherty, Simon ;
Knight, Julian G. ;
Smyth, Catherine H. ;
Harrington, Ross W. ;
Clegg, William .
ORGANIC LETTERS, 2007, 9 (23) :4925-4928
[8]   Resolution of BIPHEP on Rh with a chiral diene auxiliary [J].
Faller, J. W. ;
Wilt, Jeremy C. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (10) :2207-2212
[9]   Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): Catalytic, kinetic resolution of allyl carbonates [J].
Fischer, C ;
Defieber, C ;
Suzuki, T ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1628-1629
[10]  
FREUDENBERG K, 1933, STEREOCHEMIE ED, P803