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

Pauline Elizabeth Glen; James Alan Thomas O'Neill; Ai-Lan Lee

doi:10.1016/j.tet.2012.10.069

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

Pauline Elizabeth Glen, James Alan Thomas O'Neill, Ai-Lan Lee^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	57-68
Number of pages	12
Journal	Tetrahedron
Volume	69
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2012.10.069
Publication status	Published - 7 Jan 2013

Keywords

Macrocycles
Bis-oxazolines
Oxidative Heck
CuAAC click
Cadiot-Chodkiewicz
Rotaxane
HECK-TYPE REACTION
CLICK CHEMISTRY
CYCLOPROPANATION REACTIONS
BIS(OXAZOLINE) LIGANDS
ASYMMETRIC CATALYSIS
MOLECULAR SHUTTLES
C-2-SYMMETRIC LIGANDS
COMPLEXES
CATENANES
RESOLUTION

Access to Document

10.1016/j.tet.2012.10.069

Cite this

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title = "Synthesis of a C1-symmetric box macrocycle and studies toward active template synthesis of mechanically planar chiral rotaxanes",

abstract = "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.",

keywords = "Macrocycles, Bis-oxazolines, Oxidative Heck, CuAAC click, Cadiot-Chodkiewicz, Rotaxane, HECK-TYPE REACTION, CLICK CHEMISTRY, CYCLOPROPANATION REACTIONS, BIS(OXAZOLINE) LIGANDS, ASYMMETRIC CATALYSIS, MOLECULAR SHUTTLES, C-2-SYMMETRIC LIGANDS, COMPLEXES, CATENANES, RESOLUTION",

author = "Glen, \{Pauline Elizabeth\} and O'Neill, \{James Alan Thomas\} and Ai-Lan Lee",

year = "2013",

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doi = "10.1016/j.tet.2012.10.069",

language = "English",

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journal = "Tetrahedron",

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T1 - Synthesis of a C1-symmetric box macrocycle and studies toward active template synthesis of mechanically planar chiral rotaxanes

AU - Glen, Pauline Elizabeth

AU - O'Neill, James Alan Thomas

AU - Lee, Ai-Lan

PY - 2013/1/7

Y1 - 2013/1/7

N2 - 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.

AB - 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.

KW - Macrocycles

KW - Bis-oxazolines

KW - Oxidative Heck

KW - CuAAC click

KW - Cadiot-Chodkiewicz

KW - Rotaxane

KW - HECK-TYPE REACTION

KW - CLICK CHEMISTRY

KW - CYCLOPROPANATION REACTIONS

KW - BIS(OXAZOLINE) LIGANDS

KW - ASYMMETRIC CATALYSIS

KW - MOLECULAR SHUTTLES

KW - C-2-SYMMETRIC LIGANDS

KW - COMPLEXES

KW - CATENANES

KW - RESOLUTION

U2 - 10.1016/j.tet.2012.10.069

DO - 10.1016/j.tet.2012.10.069

M3 - Article

SN - 0040-4020

VL - 69

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EP - 68

JO - Tetrahedron

JF - Tetrahedron

IS - 1