Binap-silver salts as chiral catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes

被引：30

作者：

Mancebo-Aracil, Juan ^{[1
,2
]}

Martin-Rodriguez, Maria ^{[1
,2
]}

Najera, Carmen ^{[1
,2
]}

Sansano, Jose M. ^{[1
,2
]}

Costa, Paulo R. R. ^{[3
]}

de Lima, Evanoel Crizanto ^{[3
]}

Dias, Ayres G. ^{[3
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Alicante, Fac Ciencias, ISO, E-03080 Alicante, Spain

[3] Univ Fed Rio de Janeiro, Ctr Ciencias Saude, Lab Quim Biorgan, Nucleo Pesquisas Prod Nat, BR-21941590 Rio De Janeiro, Brazil

来源：

TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 22-23期

关键词：

COMPLEXES; TRIFLUOROACETATE; BINAP-GOLD(I); GLYCINE; IMINES;

D O I：

10.1016/j.tetasy.2012.10.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Binap-AgSbF6 catalyzed 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes are described and compared with analogous transformations mediated by other Binap-silver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfonyl)ethylene are suitable dipolarophiles for obtaining very good enantioselectivities, even better values are generated by a multicomponent version. There are some very interesting applications of the disulfonylated cycloadducts in the total synthesis of cis-2,5-disubstituted pyrrolidines, precursors of natural products, or valuable intermediates in the synthesis of antiviral compounds. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1596 / 1606

页数：11

共 37 条

[1] Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides [J].