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

页码：14224 / 14233

页数：10

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