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
来源：
TETRAHEDRON | 2013年 / 69卷 / 01期
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
相关论文
共 100 条
[11]   Cadiot-Chodkiewicz active template synthesis of rotaxanes and switchable molecular shuttles with weak intercomponent interactions [J].
Berna, Jose ;
Goldup, Stephen M. ;
Lee, Ai-Lan ;
Leigh, David A. ;
Symes, Mark D. ;
Teobaldi, Gilberto ;
Zerbetto, Francesco .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4392-4396
[12]   A catalytic palladium active-metal template pathway to [2]rotaxanes [J].
Berna, Jose ;
Crowley, James D. ;
Goldup, Stephen M. ;
Haenni, Kevin D. ;
Lee, Ai-Lan ;
Leigh, David A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) :5709-5713
[13]   Strategies and Tactics for the Metal-Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links [J].
Beves, Jonathon E. ;
Blight, Barry A. ;
Campbell, Christopher J. ;
Leigh, David A. ;
McBurney, Roy T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9260-9327
[14]   Synthesis of a polypseudorotaxane, polyrotaxane, and polycatenane using 'click' chemistry [J].
Bria, Marc ;
Bigot, Julien ;
Cooke, Graeme ;
Lyskawa, Joel ;
Rabani, Gouher ;
Rotello, Vincent M. ;
Woisel, Patrice .
TETRAHEDRON, 2009, 65 (01) :400-407
[15]  
Cadiot P., 1969, CHEM ACETYLENES, P597
[16]   Parallel kinetic resolution of active esters using designer oxazolidin-2-ones derived from phenylglycine [J].
Chavda, Sameer ;
Coulbeck, Elliot ;
Dingjan, Marco ;
Eames, Jason ;
Flinn, Anthony ;
Northen, Julian .
TETRAHEDRON-ASYMMETRY, 2008, 19 (13) :1536-1548
[17]   First Regio- and Enantioselective Chromium-Catalyzed Homoallenylation of Aldehydes [J].
Coeffard, Vincent ;
Aylward, Miriam ;
Guiry, Patrick J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9152-9155
[18]   Synthesis of [2]-, [3]-, and [4]rotaxanes whose axis contains two bidentate and two tridentate chelates [J].
Collin, Jean-Paul ;
Durot, Stephanie ;
Sauvage, Jean-Pierre ;
Trolez, Yann .
NEW JOURNAL OF CHEMISTRY, 2011, 35 (10) :2009-2012
[19]   Synthesis of [5]Rotaxanes Containing Bi- and Tridentate Coordination Sites in the Axis [J].
Collin, Jean-Paul ;
Durot, Stephanie ;
Keller, Michel ;
Sauvage, Jean-Pierre ;
Trolez, Yann ;
Cetina, Mario ;
Rissanen, Kari .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) :947-957
[20]   Templated Synthesis of Cyclic [4]Rotaxanes Consisting of Two Stiff Rods Threaded through Two Bis-macrocycles with a Large and Rigid Central Plate as Spacer [J].
Collin, Jean-Paul ;
Durola, Fabien ;
Frey, Julien ;
Heitz, Valerie ;
Reviriego, Felipe ;
Sauvage, Jean-Pierre ;
Trolez, Yann ;
Rissanen, Kari .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (19) :6840-6850
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