Template-directed synthesis employing reversible imine bond formation

Chemical Society Reviews
Cari D MeyerJ Fraser Stoddart

Abstract

The imine bond--formed by the reversible condensation of an amine and an aldehyde--and its applications as a dynamic covalent bond in the template-directed synthesis of molecular compounds, will be the focus of this tutorial review. Template-directed synthesis--or expressed another way, supramolecular assistance to covalent synthesis--relies on the use of reversible noncovalent bonding interactions between molecular building blocks in order to preorganise them into a certain relative geometry as a prelude to covalent bond formation to afford the thermodynamically preferred product. The use of this so-called dynamic covalent chemistry (DCC) in templated reactions allows for an additional amount of reversibility, further eliminating potential kinetic products by allowing the covalent bonds that are formed during the template-directed reaction to be 'proofread for errors', thus making it possible for the reaction to search out its thermodynamic minimum. The marriage of template-directed synthesis with DCC has allowed chemists to construct an increasingly complex collection of compounds from relatively simple precursors. This new paradigm in organic synthesis requires that each individual piece in the molecular self-assembly proces...Continue Reading

References

Mar 18, 1997·Proceedings of the National Academy of Sciences of the United States of America·I Huc, J M Lehn
Aug 24, 2000·Organic Letters·S RoJ F Stoddart
Jun 1, 2001·Angewandte Chemie·Peter T. GlinkDavid J. Williams
Jan 10, 2002·Nature·K OhJ S Moore
Mar 14, 2002·Proceedings of the National Academy of Sciences of the United States of America·J Fraser Stoddart, Hsian-Rong Tseng
May 23, 2002·Journal of the American Chemical Society·Tohru NishinagaJeffrey S Moore
Dec 20, 2002·Angewandte Chemie·Stuart J RowanJ Fraser Stoddart
Oct 1, 2003·Proceedings of the National Academy of Sciences of the United States of America·Jonathan R Nitschke, Jean-Marie Lehn
May 29, 2004·Science·Kelly S ChichakJ Fraser Stoddart
Dec 14, 2004·Angewandte Chemie·Jonathan R NitschkeGérald Bernardinelli
Dec 17, 2004·Journal of the American Chemical Society·Jonathan R NitschkeDavid Gérard
Jan 19, 2005·Accounts of Chemical Research·Stuart J CantrillJ Fraser Stoddart
Apr 21, 2005·Journal of the American Chemical Society·Ken C-F LeungJ Fraser Stoddart
May 12, 2005·Chemistry : a European Journal·Fabio AricóJ Fraser Stoddart
Jul 6, 2005·Chemical Communications : Chem Comm·Kelly S ChichakJ Fraser Stoddart
Jul 6, 2005·Chemical Communications : Chem Comm·Andrea J PetersJ Fraser Stoddart
Nov 10, 2005·The Journal of Organic Chemistry·Kelly S ChichakJ Fraser Stoddart
Dec 31, 2005·Angewandte Chemie·Xuejun LiuRalf Warmuth
Jun 9, 2006·Angewandte Chemie·Cari D PentecostJ Fraser Stoddart
Sep 20, 2006·Angewandte Chemie·Avril R WilliamsDavid J Williams
Oct 26, 2006·Journal of the American Chemical Society·Xuejun Liu, Ralf Warmuth
Nov 18, 2006·Angewandte Chemie·Cari D PentecostJ Fraser Stoddart
Jan 25, 2007·Chemistry : a European Journal·David Schultz, Jonathan R Nitschke
Mar 28, 2007·Journal of the American Chemical Society·C Scott HartleyJeffrey S Moore
May 23, 2007·Organic Letters·Claire R YatesJ Fraser Stoddart
Apr 17, 2001·Angewandte Chemie·David A LeighJenny K Y Wong

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Citations

Aug 22, 2013·Accounts of Chemical Research·Santiago V Luis, I Alfonso
Jun 23, 2011·Chemical Reviews·Ross S ForganJ Fraser Stoddart
Apr 19, 2011·Journal of the American Chemical Society·Anton GranzhanKay Severin
Jun 7, 2011·Journal of the American Chemical Society·J Frantz Folmer-Andersen, Jean-Marie Lehn
Aug 5, 2011·Journal of the American Chemical Society·M Shema-MizrachiN G Lemcoff
Nov 5, 2011·Journal of the American Chemical Society·Alexandre G L OliveJosef Michl
Feb 4, 2012·Journal of the American Chemical Society·Anna K H HirschJean-Marie Lehn
Nov 17, 2011·Journal of the American Chemical Society·Chenxi ZhangWei Zhang
Feb 7, 2012·Journal of the American Chemical Society·Matthew E BelowichJ Fraser Stoddart
May 18, 2013·Journal of the American Chemical Society·Sheng-Li HuangGuo-Xin Jin
Nov 5, 2013·Journal of the American Chemical Society·Ana M CastillaJonathan R Nitschke
Dec 31, 2008·Journal of the American Chemical Society·Pim G A JanssenAlbertus P H J Schenning
Feb 19, 2009·Journal of the American Chemical Society·Burçak IçliKay Severin
Feb 12, 2009·Journal of the American Chemical Society·Sébastien Ulrich, Jean-Marie Lehn
Aug 4, 2009·Journal of the American Chemical Society·Shuichi HiraokaMitsuhiko Shionoya
Dec 5, 2009·Journal of the American Chemical Society·Valeria AmendolaEnrico Monzani
Sep 5, 2009·Journal of the American Chemical Society·Paul G ClarkRobert H Grubbs
Oct 8, 2009·Journal of the American Chemical Society·Stephen M GoldupJhenyi Wu
Feb 18, 2010·Journal of the American Chemical Society·Paul G ClarkRobert H Grubbs
Aug 27, 2011·The Journal of Organic Chemistry·Robert C Boutelle, Brian H Northrop
Nov 2, 2013·The Journal of Organic Chemistry·Surisadai I Moreno-OlivaresJorge Tiburcio
Aug 24, 2010·Nature Chemistry·Tom HasellAndrew I Cooper
Feb 24, 2011·Nature Communications·Feng LiGeorge V Meehan
Aug 10, 2013·Nature Communications·Takaya TerashimaMitsuo Sawamoto
Sep 2, 2008·Chemical Communications : Chem Comm·Simon M TuregaDouglas Philp
Nov 6, 2008·Chemical Communications : Chem Comm·Zaida Rodriguez-Docampo, Sijbren Otto
Oct 3, 2008·Chemical Communications : Chem Comm·Michael Mastalerz
Oct 29, 2008·Chemical Communications : Chem Comm·A Abibat SalaudeenMalcolm A Halcrow
Dec 3, 2008·Chemical Communications : Chem Comm·Yi JiangDeyue Yan
Jun 27, 2009·Chemical Communications : Chem Comm·Vittorio Saggiomo, Ulrich Lüning
Aug 12, 2009·Chemical Communications : Chem Comm·Niamh S MurrayThorfinnur Gunnlaugsson
Oct 21, 2009·Chemical Communications : Chem Comm·Akhil K NairDanaboyina Ramaiah
Feb 24, 2010·Chemical Communications : Chem Comm·Xin Zhao, Zhan-Ting Li
Apr 14, 2010·Chemical Communications : Chem Comm·Guillaume GodinAndreas Herrmann
Mar 30, 2011·Chemical Communications : Chem Comm·Erin L ElliottJeffrey S Moore
Oct 25, 2011·Chemical Communications : Chem Comm·Marta Dal MolinLeonard J Prins
Apr 10, 2014·Journal of the American Chemical Society·Shijun LiPeter J Stang
Apr 18, 2014·Accounts of Chemical Research·Yinghua JinWei Zhang
Apr 15, 2015·International Journal of Molecular Sciences·Ken Cham-Fai LeungWing-Yan Wong

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