syn-selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu-Sm-Schiff base complex

被引:217
作者
Handa, Shinya [1 ]
Gnanadesikan, Vijay [1 ]
Matsunaga, Shigeki [1 ]
Shibasaki, Masakatsu [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan
关键词
D O I
10.1021/ja0701560
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
syn-Selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu/Sm/Schiff base complex are described. The present method is complementary to the previously reported methods, and products were obtained in high syn-selectivity (> 20:1), yield (99-62%), and enantioselectivity (98-83% ee). Both Cu and Sm metals, aligned suitably in a dinucleating Schiff base ligand, were essential to realize high synselectivity.
引用
收藏
页码:4900 / +
页数:3
相关论文
共 28 条
[21]   The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids:: Enantioselective synthesis of β-amino acids [J].
Song, Jun ;
Wang, Yi ;
Deng, Li .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6048-6049
[22]   A direct catalytic asymmetric Mannich-type reaction via a dinuclear zinc catalyst:: Synthesis of either anti- or syn-α-hydroxy-β-amino ketones [J].
Trost, BM ;
Jaratjaroonphong, J ;
Reutrakul, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2778-2779
[23]   Asymmetric catalytic aza-Henry reactions leading to 1,2-diamines and 1-,2-diaminocarboxylic acids [J].
Westermann, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (02) :151-153
[24]   Bifunctional-thiourea-catalyzed diastereo- and enantioselective aza-Henry reaction [J].
Xu, XN ;
Furukawa, T ;
Okino, T ;
Miyabe, H ;
Takemoto, Y .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (02) :466-476
[25]  
Yamada K, 1999, ANGEW CHEM INT EDIT, V38, P3504, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3504::AID-ANIE3504>3.0.CO
[26]  
2-E
[27]  
Yamada K, 2001, SYNLETT, P980
[28]   Highly enantioselective thiourea-catalyzed nitro-Mannich reactions [J].
Yoon, TP ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :466-468