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Synthesis 2012; 44(19): 3095-3107
DOI: 10.1055/s-0032-1317031
paper
© Georg Thieme Verlag Stuttgart · New York

Template Synthesis of endo-Functionalized Macrocycles Using Boronic Esters of Tetraols Followed by Ring-Closing Metathesis[1]

Dennis Stoltenberg
a   Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany, Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
,
Christian Näther
b   Institut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany, Fax: +49(431)8801520   Email: cnaether@ac.uni-kiel.de
,
Hajo Meyer
a   Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany, Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
,
Svea Machay
a   Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany, Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
,
Sonja Lüthje
a   Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany, Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
,
Ulrich Lüning*
a   Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstraße 40, 24098 Kiel, Germany, Fax: +49(431)8801558   Email: luening@oc.uni-kiel.de
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Further Information

Publication History

Received: 21 June 2012

Accepted after revision: 12 July 2012

Publication Date:
20 August 2012 (online)

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Abstract

Several stiff tetraols can be used as templates for the synthesis of bimacrocyclic diboronic esters. The endo-boronic acid functionalities can be substituted to give new endo-functionalized macrocycles (phenols, biphenyls) or new bimacrocycles (concave pyridines or concave 1,10-phenanthrolines).

Key words

macrocycles - supramolecular chemistry - receptors - boronic acids - molecular recognition
 

  • References

  • 1 Concave Reagents, part 62. Part 61: Lüning U, Liebig T. Eur. J. Org. Chem. 2012; 1346
  • 2 (a) New address: Novamelt GmbH, Wehr, Germany. (b) New address: Heinrich-Heine-Universität, Düsseldorf, Germany.
  • 3 Steed JW, Atwood JL. Supramolecular Chemistry . 2nd ed. John Wiley & Sons; Chichester: 2009
    CrossrefGoogle Scholar
  • 4 Dietrich B, Viout P, Lehn J.-M. Macrocyclic Chemistry . VCH; Weinheim: 1993
    Google Scholar
  • 5 For instance high dilution: Vögtle F. Chem.-Ztg. 1972; 96: 396
  • 6 Templated Organic Synthesis . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 2000
    Google Scholar
  • 7 Templates in Chemistry I . In Topics in Current Chemistry . Vol. 248. Schalley CA, Vögtle F, Dötz KH. Springer; Berlin: 2004
    Google Scholar
  • 8 Templates in Chemistry II . In Topics in Current Chemistry . Vol. 249. Schalley CA, Vögtle F, Dötz KH. Springer; Berlin: 2005
    Google Scholar
  • 9 Templates in Chemistry III . In Topics in Current Chemistry . Vol. 287. Broekmann P, Dötz KH, Schalley CA. Springer; Berlin: 2009
    Google Scholar
  • 10 Boronic Acids . Hall DG. Wiley-VCH; Weinheim: 2005
    CrossrefGoogle Scholar
  • 11 Severin K. Dalton Trans. 2009; 5254
  • 12 Lüthje S, Bornholdt C, Lüning U. Eur. J. Org. Chem. 2006; 909
  • 13 Stoltenberg D, Lüthje S, Winkelmann O, Näther C, Lüning U. Eur. J. Org. Chem. 2011; 5845
  • 14 Hart H, Lai CY, Chukuemeka Nwokogu G, Shamouilian S. Tetrahedron 1987; 43: 5203
    Crossref
  • 15 Ashton PR, Brown GR, Isaacs NS, Giuffrida D, Kohnke FH, Mathias JP, Slawin AM. Z, Smith DR, Stoddart JF, Williams DJ. J. Am. Chem. Soc. 1992; 114: 6330
    Crossref
  • 16 Zemplén G, Kunz A. Ber. Dtsch. Chem. Ges. 1923; 56: 1705
    Crossref
  • 17 Lüning U, Müller M. Chem. Ber. 1990; 123: 643
    Crossref
  • 18 Due to an impurity in the decenyl side chains, the product contained some isomerized decenyl chains; full characterization was therefore not possible.
  • 19 A recent review on concave reagents: Lüning U. Molecular Encapsulation . Bringer UH, Mieusset J.-L. John Wiley & Sons; Chichester: 2010: 175-199
    Google Scholar

      • The amplification of molecules from an equilibrium of products is a central task in dynamic combinatorial chemistry. For overviews see:
    • 20a Dynamic Combinatorial Chemistry . Reek JN. H, Otto S. Wiley-VCH; Weinheim: 2010
      CrossrefGoogle Scholar
    • 20b Corbett PT, Leclaire J, Vial L, West KR, Wietor J.-L, Sanders JK. M, Otto S. Chem. Rev. 2006; 106: 3652
      CrossrefPubMed
    • 20c Dynamic Combinatorial Chemistry. In Drug Discovery, Bioorganic Chemistry, and Materials Science. Miller BL. John Wiley & Sons; Hoboken: 2010
      Google Scholar
  • 21 Toyota S, Woods CR, Benagalia M, Siegel JS. Tetrahedron Lett. 1998; 39: 2697
    Crossref
  • 22 Lüthje S. Dissertation . Christian-Albrechts-Universität zu Kiel; Germany: 2006
    Google Scholar