Binap-Gold(I) versus Binap-Silver Trifluoroacetate Complexes as Catalysts in 1,3-Dipolar Cycloadditions of Azomethine Ylides

被引：45
|
作者：
Martin-Rodriguez, Maria [1 ]
Najera, Carmen [1 ]
Sansano, Jose M. [1 ]
de Cozar, Abel [2 ]
Cossio, Fernando P. [2 ]
机构：
[1] Univ Alicante, Inst Sintesis Organ, E-03080 Alicante, Spain
[2] Univ Basque Country, Inst Fac Quim, San Sebastian 20018, Spain
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 50期
关键词：
asymmetric synthesis; azomethine; cycloaddition; gold; silver; GOLD CATALYSIS; LIGAND; MECHANISM; POLYMER; IMINES; ESTERS;
D O I：
10.1002/chem.201101606
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The 1,3-dipolar cycloaddition between azomethine ylides and alkenes is efficiently catalysed by [{(Sa)-Binap-Au(tfa)}(2)] (Binap=2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tfa=trifluoroacetyl). Maleimides, 1,2-bis(phenylsulfonyl) ethylene, chalcone and nitrostyrene were suitable dipolarophiles even when using sterically hindered 1,3-dipole precursors. The results obtained in these transformations improve the analogous ones obtained in the same reactions catalysed by [Binap-Ag(tfa)]. In addition, computational studies have also been carried out to demonstrate both the high enantioselectivity exhibited by the chiral gold(I) complex, and the non-linear effect observed in this transformation.
引用
收藏
页码：14224 / 14233
页数：10
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