A new pyridyl bis(oxazoline) ligand prepared from D-glucosamine for asymmetric alkynylation of imines

被引：50
作者：
Irmak, Mustafa [1 ]
Boysen, Mike M. K. [1 ]
机构：
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 03期
关键词：
alkynylation; asymmetric catalysis; carbohydrates; copper; ligand design; oxazolines;
D O I：
10.1002/adsc.200700592
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A new carbohydrate-based pyridyl bis(oxazoline) has been prepared from D-glucosamine via simple steps. With this ligand enantioselectivities up to 99% were achieved in copper(I)-catalysed alkynylations of imines.
引用
收藏
页码：403 / 405
页数：3
相关论文
共 32 条
[1]   Enantioselective addition of phenyl and alkyl acetylenes to imines catalyzed by chiral Cu(I) complexes [J].
Benaglia, M ;
Negri, D ;
Dell'Anna, G .
TETRAHEDRON LETTERS, 2004, 45 (47) :8705-8708
[2]   Enantioselective one-pot three-component synthesis of propargylamines [J].
Bisai, Alakesh ;
Singh, Vinod K. .
ORGANIC LETTERS, 2006, 8 (11) :2405-2408
[3]   Carbohydrates as synthetic tools in organic chemistry [J].
Boysen, Mike M. K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (31) :8649-8659
[4]   C1 and C2-symmetric carbohydrate phosphorus ligands in asymmetric catalysis [J].
Castillón, S ;
Claver, C ;
Díaz, Y .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (08) :702-713
[5]   Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes [J].
Colombo, F ;
Benaglia, M ;
Orlandi, S ;
Usuelli, F ;
Celentano, G .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2064-2070
[6]   Pyridine-2,6-bis(oxazolines), helpful ligands for asymmetric catalysts [J].
Desimoni, G ;
Faita, G ;
Quadrelli, P .
CHEMICAL REVIEWS, 2003, 103 (08) :3119-3154
[7]   C2-symmetric chiral bis(oxazoline) ligands in asymmetric catalysis [J].
Desimoni, Giovanni ;
Faita, Giuseppe ;
Jorgensen, Karl Anker .
CHEMICAL REVIEWS, 2006, 106 (09) :3561-3651
[8]   Ligands derived from carbohydrates for asymmetric catalysis [J].
Diéguez, M ;
Pàmies, OP ;
Claver, C .
CHEMICAL REVIEWS, 2004, 104 (06) :3189-3215
[9]   Carbohydrate derivative ligands in asymmetric catalysis [J].
Diéguez, M ;
Pàmies, O ;
Ruiz, A ;
Díaz, Y ;
Castillón, S ;
Claver, C .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2165-2192
[10]   Rh2[MTPA]4, a dirhodium complex as NMR auxiliary for chiral recognition [J].
Duddeck, H .
CHEMICAL RECORD, 2005, 5 (06) :396-409
1234