Binap-gold(I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1,3-dipolar cycloaddition of azomethine ylides

被引：32
|
作者：
Martin-Rodriguez, Maria
Najera, Carmen [1 ]
Sansano, Jose M.
Wu, Feng-Liu
机构：
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 9-10期
关键词：
ASYMMETRIC CATALYSIS; STEREOSELECTIVE-SYNTHESIS; COMPLEXES; ALKENES; DERIVATIVES;
D O I：
10.1016/j.tetasy.2010.06.011
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Highly enantioselective 1,3-dipolar cycloadditions of amino acid-derived azomethine ylides with alkenes have been performed, for the first time, under gold-catalysis using (S-a)- or (R-a)-Binap-gold(I) trifluoroacetate complexes, with the cationic Binap-gold acting as a Lewis acid and the counteranion as a base. Maleimides and trans-1,2-bis(phenylsulfonyl)ethylene were reacted with imino esters at room temperature in the absence of a base to afford, in very good yields, the corresponding polysubstituted prolines with total endo-diastereoselection and higher enantioselectivities than the Binap-silver trifluoroacetate complex. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1184 / 1186
页数：3
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