Chiral monometallic lanthanide(III) salt complexes are arrayed acid-base networks for enantioselective catalysis:: a direct, nitroaldol (Henry) reaction

被引:50
作者
Saá, JM [1 ]
Tur, F [1 ]
González, J [1 ]
Vega, M [1 ]
机构
[1] Univ Illes Balears, Dept Quim, Palma de Mallorca 07122, Spain
关键词
D O I
10.1016/j.tetasy.2005.11.014
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Shelf stable, but kinetically labile, highly symmetric, 3:1 complexes of 3,3'-bis-diethylaminomethyl-2,2'-dihydroxy-1,1'-dinaphthalene 1 ('binolam') with lanthanide(III) triflates are easily available compounds possessing an extended array of acid and base sites. The enantiopure lanthanum derivative is especially suited to catalyze the direct nitroaldol (Henry) reaction enantioselectively. Added non-aqueous base accelerates the reaction. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:99 / 106
页数:8
相关论文
共 45 条
[1]   ENERGY-ADJUSTED ABINITIO PSEUDOPOTENTIALS FOR THE 2ND AND 3RD ROW TRANSITION-ELEMENTS [J].
ANDRAE, D ;
HAUSSERMANN, U ;
DOLG, M ;
STOLL, H ;
PREUSS, H .
THEORETICA CHIMICA ACTA, 1990, 77 (02) :123-141
[2]  
[Anonymous], COMPREHENSIVE ASYMME
[3]  
[Anonymous], COMPREHENSIVE ASYMME
[4]   Chiral lanthanide complexes: Coordination chemistry and applications [J].
Aspinall, HC .
CHEMICAL REVIEWS, 2002, 102 (06) :1807-1850
[5]   Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes [J].
Aspinall, HC ;
Greeves, N ;
Smith, PM .
TETRAHEDRON LETTERS, 1999, 40 (09) :1763-1766
[6]   Binolam-AlCl:: A two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates [J].
Baeza, A ;
Nájera, C ;
Sansano, JM ;
Saá, JM .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (13) :3849-3862
[7]   MILD LEWIS ACID CATALYSIS - EU(FOD)3-MEDIATED HETERO-DIELS-ALDER REACTION [J].
BEDNARSKI, M ;
DANISHEFSKY, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3716-3717
[8]   CHIRAL INDUCTION IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES [J].
BEDNARSKI, M ;
MARING, C ;
DANISHEFSKY, S .
TETRAHEDRON LETTERS, 1983, 24 (33) :3451-3454
[9]   POTENTIOMETRIC, CALORIMETRIC, AND SOLUTION NMR-STUDIES OF A TRIDENTATE LIGAND WHICH HAS A MARKED PREFERENCE FOR FORMATION OF BIS(LIGAND) VERSUS MONO(LIGAND) LANTHANIDE COMPLEXES AND WHICH EXHIBITS HIGH SELECTIVITY FOR HEAVIER LANTHANIDES [J].
CARAVAN, P ;
HEDLUND, T ;
LIU, S ;
SJOBERG, S ;
ORVIG, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) :11230-11238
[10]   Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters [J].
Christensen, C ;
Juhl, K ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2001, (21) :2222-2223