Role of the peri-effect in synthesis and reactivity of highly substituted naphthaldehydes: A novel backbone amide linker for solid-phase synthesis

Organic and Biomolecular Chemistry

Volumn 3, Issue 3, 2005, Pages 508-514

  Pittelkow, Michael ^a   Boas, Ulrik ^a,b   Jessing, Mikkel ^a   Jensen, Knud J ^b   Christensen, Jørn B ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CRYSTAL STRUCTURE; ELECTRONIC PROPERTIES; HYDROLYSIS; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE; POLYCYCLIC AROMATIC HYDROCARBONS; X RAYS;

BACKBONE AMIDE LINKER (BAL); DEMETHYLATION; NAPTHALDEHYDES; TRIFLUOROACETIC ACID (TFA);

ALDEHYDES;

ALDEHYDE; AMIDE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; AMIDES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES;

EID: 14244270094     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412971g     Document Type: Article

References (44)

1. (a) R. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149;
2. (b) R. L. Letsinger and M. J. Kornet, J. Am. Chem. Soc., 1963, 85, 3045.
3. (a) M. Goodman, A. Felix, L. Moroder, C. Toniolo, ed., Houben-Weyl. Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart-New York, 2002, vol. E22a;
4. (b) L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555.
5. R. B. Merrifield, Angew. Chem., Im. Ed. Engt., 1985, 24, 799.
6. For general reviews on linkers see: (a) M. F. Songster and G. Barany, Methods Enzymol., 1997, 289, 126; (b) B. J. Backes and J. A. Ellman, Curr. Opin. Chem. Biol., 1997, 1, 86; (c) I. W. James, Tetrahedron, 1999, 55, 4855; (d) P. Virta, J. Katajisto, T. Niittyma and H. Lönnberg, Tetrahedron, 2003, 59, 5137.
7. For general reviews on linkers see: (a) M. F. Songster and G. Barany, Methods Enzymol., 1997, 289, 126; (b) B. J. Backes and J. A. Ellman, Curr. Opin. Chem. Biol., 1997, 1, 86; (c) I. W. James, Tetrahedron, 1999, 55, 4855; (d) P. Virta, J. Katajisto, T. Niittyma and H. Lönnberg, Tetrahedron, 2003, 59, 5137.
8. For general reviews on linkers see: (a) M. F. Songster and G. Barany, Methods Enzymol., 1997, 289, 126; (b) B. J. Backes and J. A. Ellman, Curr. Opin. Chem. Biol., 1997, 1, 86; (c) I. W. James, Tetrahedron, 1999, 55, 4855; (d) P. Virta, J. Katajisto, T. Niittyma and H. Lönnberg, Tetrahedron, 2003, 59, 5137.
9. For general reviews on linkers see: (a) M. F. Songster and G. Barany, Methods Enzymol., 1997, 289, 126; (b) B. J. Backes and J. A. Ellman, Curr. Opin. Chem. Biol., 1997, 1, 86; (c) I. W. James, Tetrahedron, 1999, 55, 4855; (d) P. Virta, J. Katajisto, T. Niittyma and H. Lönnberg, Tetrahedron, 2003, 59, 5137.
10. (a) K. J. Jensen, M. F. Songster, J. Vágner, J. Alsina, F. Alberitio and G. Barany, J. Am. Chem. Soc., 1998, 120, 5441;
11. (b) Initial accounts: K. J. Jensen, M. F. Songster, J. Vágner, J. Alsina, F. Albericio and G. Barany, in Peptides: Chemistry, Structure and Biology, Proceedings of the 14th American Peptide Symposium, Columbus, Ohio, June 18-23, 1995, ed., P. T. P. Kaumaya and R. S. Hodges, Mayflower Scientific, Kingswinford, UK, 1996, p. 30;
12. (c) K. J. Jensen, M. F. Songster, J. Alsina, J. Vágner, F. Albericio and G. Barany, in Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries: Peptides, Proteins and Nucleic Acids - Small Molecule Organic Chemical Diversity, Collected Papers, 4th International Symposium, Edinburgh, Sept. 12-16, 1995, ed., R. Epton, Mayflower Scientific, Birmingham, UK, 1996, p. 187.
13. (a) C. G. Boojamra, K. M. Burow and J. A. Ellman, J. Org. Chem., 1995, 60, 5742;
14. (b) C. G. Boojamra, K. M. Burow, L. A. Thompson and J. A. Ellman, J. Org. Chem., 1997, 62, 1240.
15. For reviews of BAL handles, see: (a) J. Alsina, K. J. Jensen, F. Albericio and G. Barany, Chem. Eur. J., 1999, 5, 2787; (b) J. Alsina, K. J. Jensen, M. F. Songster, J. Vágner, F. Albericio and G. Barany, in Solid-phase Organic Synthesis, Vol. 1, ed. A. W. Czarnik, John Wiley & Sons, New York, 2001, pp. 121.
16. For reviews of BAL handles, see: (a) J. Alsina, K. J. Jensen, F. Albericio and G. Barany, Chem. Eur. J., 1999, 5, 2787; (b) J. Alsina, K. J. Jensen, M. F. Songster, J. Vágner, F. Albericio and G. Barany, in Solid-phase Organic Synthesis, Vol. 1, ed. A. W. Czarnik, John Wiley & Sons, New York, 2001, pp. 121.
17. (a) G. T. Bourne, W. D. F. Meutermans, P. F. Alewood, R. P. McGeary, M. Scanlon, A. A. Watson and M. L. Smythe, J. Org. Chem., 1999, 64, 3095.
18. (a) E. E. Swayze, Tetrahedron Lett., 1997, 38, 8465;
19. (b) A. M. Fivush and T.M. Wilson, Tetrahedron Lett., 1997, 38, 7151;
20. (c) D. Sarantakis and J. J. Bicker, Tetrahedron Lett., 1997, 38, 7325;
21. (d) M. F. Gordeev, G. W. Luehr, H. C. Hui, E. M. Gordon and D. V. Patel, Tetrahedron, 1998, 54, 15879.
22. T. Okayama, A. Burritt and V. J. Hruby, Org. Lett., 2000, 2, 1787.
23. (a) K. G. Estep, C. E. Neipp, L. M. Stramiello-Stephens, M. D. Adam, M. P. Allen, S. Robinson and E. J. Roskamp, J. Org. Chem., 1998, 63, 5300;
24. (b) J. J. Scicinski, M. S. Congreve and S. V. Ley, J. Comb. Chem., 2004, 6, 375.
25. For preliminary accounts of our thiophene based T-BAL handle, see: (a) U. Boas, Ph.D. Thesis, University of Copenhagen, Copenhagen, Denmark, 2002; (b) U. Boas, J. Brask, J. B. Christensen and K. J. Jensen, in Peptides 2002, Proceedings of the 27th European Peptide Symposium, Sorrento, Italy, Aug. 31-Sept. 6, 2002, ed., E. Benedetti and C. Pedone, Edizioni Ziino, Castellammare di Stabia, Italy, 2002, p. 50.
26. For preliminary accounts of our thiophene based T-BAL handle, see: (a) U. Boas, Ph.D. Thesis, University of Copenhagen, Copenhagen, Denmark, 2002; (b) U. Boas, J. Brask, J. B. Christensen and K. J. Jensen, in Peptides 2002, Proceedings of the 27th European Peptide Symposium, Sorrento, Italy, Aug. 31-Sept. 6, 2002, ed., E. Benedetti and C. Pedone, Edizioni Ziino, Castellammare di Stabia, Italy, 2002, p. 50.
27. (a) A. Faldt, M. J. Pedersen, T. P. Krogh, L. Hviid and J. B. Christensen, Synth. Met., 1998, 94, 307;
28. (b) B. W. Laursen, F. C. Krebs, M. F. Nielsen, K. Bechgaard, J. B. Christensen and N. Harrit, J. Am. Chem. Soc., 1998, 120, 12255.
29. (a) U. Boas, J. B. Christensen and K. J. Jensen, in Peptides 2000, Proceedings of the 26th European Peptide Symposium, Montpellier, France, Sept. 10-15, 2000, Meeting Date 2000, ed., J. Martinez and J.-A. Fehrentz, Editions EDK, Paris, 2001, p. 197;
30. (b) U. Boas, J. B. Christensen and K. J. Jensen, J. Comb. Chem., 2004, 6, 497.
31. A. Bader, Adventures of a Chemist Collector, Weidenfeld & Nicolson, London, 1995.
32. (a) For a general review on the peri-eflisct in naphthalenes, sec: V. Balasubramaniyan, Chem. Rev., 1966, 66, 567; (b) For a recent example, see: A. Karacar, M. Freytag, H. Thönnesen, P. G. Jones, R. Bartsch and R. Schmutzler, J. Organomet. Chem., 2002, 68, 643.
33. (a) For a general review on the peri-eflisct in naphthalenes, sec: V. Balasubramaniyan, Chem. Rev., 1966, 66, 567; (b) For a recent example, see: A. Karacar, M. Freytag, H. Thönnesen, P. G. Jones, R. Bartsch and R. Schmutzler, J. Organomet. Chem., 2002, 68, 643.
34. C. B. de Koning, R. L. Rousseau and W. A. L. van Otterlo, Tetrahedron, 2003, 59, 7.
35. Our procedure is similar to: K. Meyer, H. S. Bloch, Org. Synth. Coll. vol. 111, 631.
36. (a) K. H. Weisgaber and U. Weiss, J. Chem. Soc., Perkin Trans. 1, 1972, 83;
37. (b) P. Müller, J. Seres, K. Steiner, S. E. Helali and E. Hardegger, Helv. Chim. Acta, 1974, 57, 790;
38. (c) A. Piettre, E. Chevenier, C. Massardier, Y. Gimbert and A. E. Greene, Org. Lett., 2002, 4, 3139.
39. (a) T. Mizutani, M. Takeshi, T. Kurahashi and H. Ogoshi, J. Org. Chem., 1996, 61, 539;
40. (b) R. L. Hannan, R. B. Barber and H. Rapoport, J. Org. Chem., 1979, 44, 2153.
41. o-BAL: U. Boas, J. Brask, J. B. Christensen and K. J. Jensen, J. Comb. Chem., 2002, 4, 223.
42. B. Yang, N. Nguyen, L. Liu, G. Holland and B. Raju, J. Comb. Chem., 2000, 2, 66.
43. A. F. Pozharsldi, O. V. Ryabtsova, V. A. Ozeryanskii, A. V. Degtyarev, O. N. Kazheva, G. G. Alexandrov and O. A. Dyachenko, J. Org. Chem., 2003, 68, 10109.
44. D. S. Pedersen and C. Rosenbaum, Synthesis, 2001, 16, 2431.