Synthesis and crystallographic characterization of chiral bis-oxazoline-amides. Fine-tunable ligands for Pd-catalyzed asymmetric alkylations

被引:19
作者
Albano, Vincenzo Giulio [1 ]
Bandini, Marco [1 ]
Monari, Magda [1 ]
Marcucci, Eleonora [1 ]
Piccinelli, Fabio [1 ]
Umani-Ronchi, Achille [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
D O I
10.1021/jo060767v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New chiral chelating C-2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).
引用
收藏
页码:6451 / 6458
页数:8
相关论文
共 32 条
[1]   Controlling stereochemical outcomes of asymmetric processes by catalyst remote molecular functionalizations: Chiral diamino-oligothiophenes (DATs) as ligands in asymmetric catalysis [J].
Albano, VG ;
Bandini, M ;
Barbarella, G ;
Melucci, M ;
Monari, M ;
Piccinelli, F ;
Tommasi, S ;
Umani-Ronchi, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) :667-675
[2]   Novel chiral diamino-oligothiophenes as valuable ligands in Pd-catalyzed allylic alkylations. On the "primary" role of "secondary" interactions in asymmetric catalysis [J].
Albano, VG ;
Bandini, M ;
Melucci, M ;
Monari, M ;
Piccinelli, F ;
Tommasi, S ;
Umani-Ronchi, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1507-1512
[3]  
Belvisi L, 2000, EUR J ORG CHEM, V2000, P2563
[4]   Cyclopenta[b]thiophene-alkyloxazolines:: new nitrogen-sulfur hybrid ligands and their use in asymmetric palladium-catalyzed allylic alkylation [J].
Bonini, BF ;
Giordano, L ;
Fochi, M ;
Comes-Franchini, M ;
Bernardi, L ;
Capitò, E ;
Ricci, A .
TETRAHEDRON-ASYMMETRY, 2004, 15 (06) :1043-1051
[5]   Robust and catalytically active mono- and bis-Pd-complexes of the 'Trost modular ligand' [J].
Butts, CP ;
Crosby, J ;
Lloyd-Jones, GC ;
Stephen, SC .
CHEMICAL COMMUNICATIONS, 1999, (17) :1707-1708
[6]   Palladium complexes with chiral oxazoline ligands.: Effect of chelate size on catalytic allylic substitutions [J].
Canal, JM ;
Gómez, M ;
Jiménez, F ;
Rocamora, M ;
Muller, G ;
Duñach, E ;
Franco, D ;
Jiménez, A ;
Cano, FH .
ORGANOMETALLICS, 2000, 19 (06) :966-978
[7]  
Carpino LA, 2002, ANGEW CHEM INT EDIT, V41, P442
[8]   The role of Pd nanoparticles in ionic liquid in the Heck reaction [J].
Cassol, CC ;
Umpierre, AP ;
Machado, G ;
Wolke, SI ;
Dupont, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3298-3299
[9]   Total synthesis of sequential retro-peptide oligomers [J].
Ceretti, S ;
Luppi, G ;
De Pol, S ;
Formaggio, F ;
Crisma, M ;
Toniolo, C ;
Tomasini, C .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (20) :4188-4196
[10]   Ligand design in coordination chemistry: approaches to new catalysts, new materials, and a more sustainable environment [J].
Elsevier, CJ ;
Reedijk, J ;
Walton, PH ;
Ward, MD .
DALTON TRANSACTIONS, 2003, (10) :1869-1880