Synthesis of a C-1-symmetric Box macrocycle and studies towards active-template synthesis of mechanically planar chiral rotaxanes

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 achievin...

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 1; pp. 57 - 68
Main Authors Glen, Pauline E., O'Neill, James A. T., Lee, Ai-Lan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 07.01.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COMPLEX
DESIGN
CuAAC click
HECK-TYPE REACTION
ASYMMETRIC-SYNTHESIS
BIS(OXAZOLINE) LIGANDS
RESOLUTION
MOLECULAR SHUTTLES
C-2-SYMMETRIC LIGANDS
Macrocycles
CATENANES
Cadiot-Chodkiewicz
Oxidative Heck
Bis-oxazolines
CATALYSTS
Rotaxane
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Summary: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.
Bibliography:researchfish
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.10.069