One-shot preparation of an inherently chiral trifunctional calix[4]arene from an easily available cone-triformylcalix[4]arene

Organic and Biomolecular Chemistry

Volumn 11, Issue 22, 2013, Pages 3642-3648

  Ciaccia, Maria ^a   Tosi, Irene ^b   Cacciapaglia, Roberta ^a   Casnati, Alessandro ^b   Baldini, Laura ^b   Di Stefano, Stefano ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUPS; HYDROGEN BONDS; SCAFFOLDS;

ARENE DERIVATIVES; CALIXARENES; CALIX[4]ARENES; CHIRAL DISCRIMINATION; DISPROPORTIONATIONS; HYDROXYL GROUPS; IMINE BONDS; MULTIFUNCTIONAL DEVICES;

AMINO ACIDS;

EID: 84877726190     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c3ob40355f     Document Type: Article

References (37)

1. C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, 1989
2. C. D. Gutsche, Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, 1998
3. Calixarenes: A Versatile Class of Macrocyclic Compounds, ed., J. Vicens, and, V. Böhmer, Kluwer Academic Publishers, Dordrecht, 1991
4. Calixarenes in Action, ed., L. Mandolini, and, R. Ungaro, Imperial College Press, London, 2000
5. Calixarenes 2001, ed., Z. Asfari, V. Böhmer, J. Harrowfield, and, J. Vicens, Kluwer Academic Publishers, Dordrecht, 2001
6. Calixarenes in the Nanoworld, ed., J. Vicens, and, J. Harrowfield, Springer, Dordrecht, 2006
7. A. Casnati F. Sansone R. Ungaro Acc. Chem. Res. 2003 36 246 254
8. S. E. Matthews P. D. Beer Supramol. Chem. 2005 17 411 435
9. L. Baldini A. Casnati F. Sansone R. Ungaro Chem. Soc. Rev. 2007 36 254 266
10. J. S. Kim D. T. Quang Chem. Rev. 2007 107 3780 3799
11. S. M. Biros J. Rebek Jr Chem. Soc. Rev. 2007 36 93 104
12. W. Maes W. Dehaen Chem. Soc. Rev. 2008 37 2393 2402
13. A. W. Coleman S. Jebors P. Shahgaldian G. S. Ananchenko J. A. Ripmeester Chem. Commun. 2008 2291 2303
14. D. M. Homden C. Redshaw Chem. Rev. 2008 108 5086 5130
15. F. Sansone L. Baldini A. Casnati R. Ungaro New J. Chem. 2010 34 2715 2728
16. S. André C. Grandjean F.-M. Gautier S. Bernardi F. Sansone H.-J. Gabius R. Ungaro Chem. Commun. 2011 47 6126 6128
17. H. Zhou D.-A. Wang L. Baldini E. Ennis R. Jain A. Carie S. M. Sebti A. D. Hamilton Org. Biomol. Chem. 2006 4 2376 2386
18. D. Arosio M. Fontanella L. Baldini L. Mauri A. Bernardi A. Casnati F. Sansone R. Ungaro J. Am. Chem. Soc. 2005 127 3660 3661
19. F. Sansone A. Casnati Chem. Soc. Rev. 2013 10.1039/c2cs35437c
20. V. Bagnacani V. Franceschi L. Fantuzzi A. Casnati G. Donofrio F. Sansone R. Ungaro Bioconjugate Chem. 2012 23 993 1002
21. R. Salvio A. Casnati L. Mandolini F. Sansone R. Ungaro Org. Biomol. Chem. 2012 10 8941 8943
22. L. Monnereau D. Sémeril D. Matt Eur. J. Org. Chem. 2012 2786 2791
23. L. Baldini R. Cacciapaglia A. Casnati L. Mandolini R. Salvio F. Sansone R. Ungaro J. Org. Chem. 2012 77 3381 3389
24. R. Cacciapaglia, S. Di Stefano and L. Mandolini, Reactivity control by calixarenes, in Molecular Encapsulation: Organic Reactions in Constrained Systems, ed., U. H. Brinker, and, J.-L. Mieusset, John Wiley & Sons, New York, 2010, ch. 8, pp. 201-225
25. D. M. Homden C. Redshaw Chem. Rev. 2008 108 5086 5130
26. S. Shirakawa A. Moriyama S. Shimizu Eur. J. Org. Chem. 2008 5957 5964
27. V. Böhmer F. Marschollek L. Zetta J. Org. Chem. 1987 52 3200 3205
28. S. Shirakawa T. Kimura S. Murata S. Shimizu J. Org. Chem. 2009 74 1288 1296
29. Y.-S. Zheng J. Luo J. Inclusion Phenom. Macrocyclic Chem. 2011 71 35 56
30. M. J. McIldowie M. Mocerino M. I. Ogden Supramol. Chem. 2010 22 13 39
31. A. Dalla Cort L. Mandolini C. Pasquini L. Schiaffino New J. Chem. 2004 28 1198 1199
32. M. Galli J. A. Berrocal S. Di Stefano R. Cacciapaglia L. Mandolini L. Baldini A. Casnati F. Ugozzoli Org. Biomol. Chem. 2012 10 5109 5112
33. M. Ciaccia R. Cacciapaglia P. Mencarelli L. Mandolini S. Di Stefano Chem. Sci. 2013 4 2253 2261
34. L. Stryer, Biochemistry, W. H. Freeman and Company, New York, 4th edn, 1995
35. D. J. Hupe, Enzyme reactions involving imine formation, in The Chemistry of Enzyme Action, ed., M. I. Page, Elsevier Science Publisher, New York, 1984, pp. 271-299
36. M. van Dijk T. M. Postma D. T. S. Rijkers R. M. J. Liskamp C. F. van Nostrum W. E. Hennink Polymer 2010 51 2479 2485
37. P. Molenveld W. M. G. Stikvoort H. Kooijman A. L. Spek J. F. J. Engbersen D. N. Reinhoudt J. Org. Chem. 1999 64 3896 3906