PipPhos and MorfPhos: Privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation

被引:165
作者
Bernsmann, H
van den Berg, M
Hoen, R
Minnaard, AJ
Mehler, G
Reetz, MT
De Vries, JG
Feringa, BL
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
[2] DSM Res & Patents, Life Sci Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands
[3] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/jo048374o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A library of 20 monodentate phosphoramidite ligands has been prepared and applied in rhodium-catalyzed asymmetric hydrogenation. This resulted in the identification of two ligands, PipPhos and MorfPhos, that afford excellent and in several cases unprecedented enantioselectivities in the hydrogenation of N-acyldehydroamino acid esters, dimethyl itaconate, acyclic N-acylenamides, and cyclic N-acylenamides. In addition, a method for the parallel enantioselectivity determination of eight acylated amines is presented.
引用
收藏
页码:943 / 951
页数:9
相关论文
共 101 条
[1]   Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].
Arnold, LA ;
Imbos, R ;
Mandoli, A ;
de Vries, AHM ;
Naasz, R ;
Feringa, BL .
TETRAHEDRON, 2000, 56 (18) :2865-2878
[2]   A FURTHER SYNTHESIS OF THE CORTICOSTEROID SIDE-CHAIN STARTING WITH A SUITABLE 17-KETONE [J].
BARTON, DHR ;
ZARD, SZ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10) :2191-2192
[3]  
Blaser H.U., 2004, ASYMMETRIC CATALYSIS
[4]   Enantioselective catalysis in fine chemicals production [J].
Blaser, HU ;
Spindler, F ;
Studer, A .
APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) :119-143
[5]   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
[6]   SIMPLE SYNTHESIS OF ENAMIDES FROM KETOXIMES [J].
BOAR, RB ;
MCGHIE, JF ;
ROBINSON, M ;
BARTON, DHR ;
HORWELL, DC ;
STICK, RV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13) :1237-1241
[7]   Dendritic phosphoramidite ligands in Rh-catalysed asymmetric hydrogenations [J].
Botman, PNM ;
Amore, A ;
van Heerbeek, R ;
Back, JW ;
Hiemstra, H ;
Reek, JNH ;
van Maarseveen, JH .
TETRAHEDRON LETTERS, 2004, 45 (31) :5999-6002
[8]   Combinatorial chemistry for ligand development in catalysis: Synthesis and catalysis screening of peptidosulfonamide tweezers on the solid phase [J].
Brouwer, AJ ;
van der Linden, HJ ;
Liskamp, RMJ .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1750-1757
[9]  
Brown J. M., 1999, COMPREHENSIVE ASYMME, V1
[10]   A three-step procedure for asymmetric catalytic reductive amidation of ketones [J].
Burk, MJ ;
Casy, G ;
Johnson, NB .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6084-6085