The design, synthesis and application of imidazolium-tagged ferrocenyl oxazoline phosphine ligands for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes: ion effect for enhancing the reactivity, stereoselectivity and recyclability

被引：19

作者：

Dai, Li ^{[1
]}

Xu, Di ^{[1
]}

Dong, Xiao ^{[1
]}

Zhou, Zhiming ^{[1
]}

机构：

[1] Beijing Inst Technol, R&D Ctr Pharmaceut, Sch Chem Engn & Environm, Beijing 100081, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 07期

基金：

中国国家自然科学基金;

关键词：

SELECTIVE 3+2 CYCLOADDITION; TRANSFER HYDROGENATION; CATALYSIS; COMPLEXES; ORIGINS; ESTERS;

D O I：

10.1016/j.tetasy.2015.02.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of imidazolium moiety tagged planar chiral ferrocenyl oxazoline phosphine (FimiOAXP) ligands were designed and synthesised. In connection with their usefulness as ligands for asymmetric 1,3-dipolar cycloadditions of azomethine ylides with nitroalkenes, the catalysts were prepared in situ by treatment of copper(I) perchlorate and FimiOAXP. In the presence of a weak base, the pyrrolidine analogues were obtained in satisfactory yields and with excellent enantioselectivities (up to 99% ee). Through the experimental and computational outcomes, ion effect between the imidazolium moiety and azomethine ylide proved to be an essential factor for the excellent enantioselectivity. Moreover, with the benefit of the imidazolium moiety, the asymmetric 1,3-dipolar cycloaddition underwent in DCM/ionic liquids combined solvent for the first time. Taking advantage of the occasion, the catalyst could be recycled and reused for at least five times. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：350 / 360

页数：11

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