Highly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes

被引:157
作者
Bandini, Marco [1 ]
Piccinelli, Fabio [1 ]
Tommasi, Simona [1 ]
Umani-Ronchi, Achille [1 ]
Ventrici, Caterina [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
D O I
10.1039/b613019d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Remarkable generality in scope of DATs/Cu catalysts for enantioselective nitroaldol reaction is described; excellent levels of stereoinduction are recorded for a range of aldehydes (ee 81-99%, 17 examples) and the possibility to employ the present catalytic system as the key step for the preparation of highly functionalized tetrahydro-isoquinolines is demonstrated.
引用
收藏
页码:616 / 618
页数:3
相关论文
共 23 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]   Structure and catalytic properties of dimeric copper(II) acetato complexes encapsulated in zeolite-Y [J].
Chavan, S ;
Srinivas, D ;
Ratnasamy, P .
JOURNAL OF CATALYSIS, 2000, 192 (02) :286-295
[4]   Asymmetric synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Rozwadowska, MD .
CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370
[5]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[6]   A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].
Evans, DA ;
Seidel, D ;
Rueping, M ;
Lam, HW ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693
[7]   Asymmetric synthesis of active pharmaceutical ingredients [J].
Farina, Vittorio ;
Reeves, Jonathan T. ;
Senanayake, Chris H. ;
Song, Jinhua J. .
CHEMICAL REVIEWS, 2006, 106 (07) :2734-2793
[8]   Efficient and enantioselective nitroaldol reaction catalyzed by copper Schiff-base complexes [J].
Gan, CS ;
Lai, GY ;
Zhang, ZH ;
Wang, ZY ;
Zhou, MM .
TETRAHEDRON-ASYMMETRY, 2006, 17 (05) :725-728
[9]  
Henry L. C. R., 1895, C. R. H. Acad. Sci, V120, P1265
[10]   MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST [J].
HUBERT, AJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :1984-&