Direct use of chiral or achiral organophosphorus boranes as pro-ligands for transition metal catalyzed reactions

被引:41
作者
Darcel, C
Kaloun, EB
Merdès, R
Moulin, D
Riegel, N
Thorimbert, S
Genêt, JP
Jugé, S
机构
[1] FRE CNRS 2126, Unite Mixte Univ Cergy Pontoise ESCOM, F-95031 Cergy Pontoise, France
[2] ENSCP, UMR 7573, Lab Synth Organ Select & Prod Nat, F-75005 Paris, France
关键词
phosphine boranes; rhodium catalysts; copper catalysts; palladium catalysts; asymmetric synthesis; catalysis; addition reaction; hydrogenation; allylation;
D O I
10.1016/S0022-328X(01)00666-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral or achiral organophosphorus borane complexes were used without isolation of the free tricoordinate P(III) ligand; thus, the borane adducts could be used either directly with metal salts to perform the catalysis, or they could be decomplexed by DABCO, or cyclooctadiene, and used in situ to generate the catalytic species. Chiral copper, palladium and rhodium complexes prepared using this method, were tested in asymmetric organometallic catalyzed 1,4-addition to 2-cyclohexenone, allylation of Schiff base and hydrogenation of alpha -acetamidocinnamic acid derivatives, respectively. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:333 / 343
页数:11
相关论文
共 113 条
[1]   The aminophosphine-phosphinites and related ligands: synthesis, coordination chemistry and enantioselective catalysis [J].
Agbossou, F ;
Carpentier, JF ;
Hapiot, F ;
Suisse, I ;
Mortreux, A .
COORDINATION CHEMISTRY REVIEWS, 1998, 178 :1615-1645
[2]  
Alexakis A, 1999, SYNLETT, P1811
[3]   AN EASY AND FAST WAY TO DETERMINE THE ENANTIOMERIC PURITY OF SUBSTITUTED CYCLANONES [J].
ALEXAKIS, A ;
FRUTOS, JC ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2431-2434
[4]   Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL [J].
Alexakis, A ;
Vastra, J ;
Burton, J ;
Benhaim, C ;
Mangeney, P .
TETRAHEDRON LETTERS, 1998, 39 (43) :7869-7872
[5]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[6]   Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].
Amatore, C ;
Jutand, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321
[7]   Mechanistic and kinetic studies of palladium catalytic systems [J].
Amatore, C ;
Jutand, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278
[8]   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
[9]   Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones [J].
Bennett, SMW ;
Brown, SM ;
Cunningham, A ;
Dennis, MR ;
Muxworthy, JP ;
Oakley, MA ;
Woodward, S .
TETRAHEDRON, 2000, 56 (18) :2847-2855
[10]  
Bergner EJ, 2000, EUR J ORG CHEM, V2000, P419, DOI 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO