CuI-fesulphos complexes:: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides

被引:108
作者
Cabrera, Silvia [1 ]
Arrayas, Ramon Gomez [1 ]
Martin-Matute, Belen [1 ]
Cossio, Fernando P. [2 ]
Carretero, Juan C. [1 ]
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, Madrid 28049, Spain
[2] Euskal Herriko Unibertsitatea, Kimika Fac, San Sebastian, Spain
关键词
D O I
10.1016/j.tet.2007.03.130
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Cu-I-Fesulphos catalyst system (<= 3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity ( 69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6587 / 6602
页数:16
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