Synthesis of a C1-symmetric Box macrocycle and studies towards active-template synthesis of mechanically planar chiral rotaxanes

被引:24
作者
Glen, Pauline E. [1 ]
O'Neill, James A. T. [1 ]
Lee, Ai-Lan [1 ]
机构
[1] Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4A5, Midlothian, Scotland
基金
英国工程与自然科学研究理事会;
关键词
Macrocycles; Bis-oxazolines; Oxidative Heck; CuAAC click; Cadiot-Chodkiewicz; Rotaxane; HECK-TYPE REACTION; BIS(OXAZOLINE) LIGANDS; C-2-SYMMETRIC LIGANDS; ASYMMETRIC-SYNTHESIS; MOLECULAR SHUTTLES; CATENANES; RESOLUTION; CATALYSTS; COMPLEX; DESIGN;
D O I
10.1016/j.tet.2012.10.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A C-1-symmetric Box macrocycle has been synthesized for the first time. The Box macrocycle along with other C-1 and C-2-symmetric Box ligands were evaluated and compared as ligands in the Cadiot-Chodkiewicz, oxidative Heck and CuAAC 'click' reactions as part of our studies towards achieving active-metal template synthesis of mechanically planar chiral rotaxanes. This study constitutes the first report of Cadiot-Chodkiewicz and CuAAC 'click' reactions using Box ligands, as well as the first dedicated study of oxidative Heck reactions using Box ligands. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:57 / 68
页数:12
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