Improved catalysis of nitrone 1,3-dipolar cycloadditions by solving the aggregation issue of the DBFOX/Ph-transition metal complexes

被引：30

作者：

Shirahase, M

Kanemasa, S

Hasegawa, M

机构：

[1] Kyushu Univ, JST, CREST, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Grad Sch Engn Sci, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 21期

关键词：

nitrone; 1.3-dipolar cycloaddition; aldehyde dipolarophile; catalyzed enantioselective reaction;

D O I：

10.1016/j.tetlet.2004.03.151

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method has been demonstrated to solve the aggregation issue Of metal complex catalysts'. Steric protection of the metal center of catalysts was effective in the cases of DBFOX/Ph-transition metal complexes by structural modification of chiral ligand. The new ligands have been successfully applied to the nitrone cycloadditions to a variety of alpha,beta-unsaturated aldehydes. Excellent enantioselectivities up to 99% ee have been demonstrated in the reactions at room temperature with a catalytic loading of 2 mol%. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4061 / 4063

页数：3

共 7 条

[1] The complete characterization of a rhodium Lewis acid-dipolarophile complex as an intermediate for the enantioselective catalytic 1,3-dipolar cycloaddition of C,N-diphenylnitrone to methacrolein [J].