Skip to main content
SpringerLink
Log in

Ugi products containing boronate esters

  • Invited Paper
  • Published:
Central European Journal of Chemistry

Abstract

The Ugi reaction with formylphenylboronic acid derivatives as the carbonyl component proceeds to give the corresponding boron-containing dipeptide derivatives (Ugi products) in good yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457 (1995)

    Article  CAS  Google Scholar 

  2. S. Gamsey, A. Miller, M.M. Olmstead, C.M. Beavers, L.C. Hirayama, S. Pradhan, R.A. Wessling, B. Singaram, J. Am. Chem. Soc. 129, 1278 (2007)

    Article  CAS  PubMed  Google Scholar 

  3. S. Goeb, R. Ziessel, Org. Lett. 9, 737 (2007)

    Article  CAS  PubMed  Google Scholar 

  4. J. Yoshino, N. Kano, T. Kawashima, Chem. Commun. 559 (2007)

  5. J. Ugolotti, S. Hellstorm, G.J.P. Britovsek, T.S. Jones, P. Hunt, A.J.P. White, Dalton Trans. 1425 (2007)

  6. W. Yang, X. Gao, B. Wang, Med. Res. Rev. 23, 346 (2003)

    Article  CAS  PubMed  Google Scholar 

  7. M.L. Stolowitz, C. Ahlem, K.A. Hughes, R.J. Kaiser, E.A. Kesicki, G. Li, K.P. Lund, S.M. Torkelson, J.P. Wiley, Bioconjugate Chem. 12, 229 (2001)

    Article  CAS  Google Scholar 

  8. S.A. Amin, F.C. Küpper, D.H. Green, W.R. Harris, C.J. Carrano, J. Am. Chem. Soc. 129, 478 (2007)

    Article  CAS  PubMed  Google Scholar 

  9. S.J. Baker, Y.-K. Zhang, T. Akama, A. Lau, H. Zhou, V. Hernandez, W. Mao, M.R.K. Alley, V. Sanders, J.J. Plattner, J. Med. Chem. 49, 4447 (2006)

    Article  CAS  PubMed  Google Scholar 

  10. T. Tran, C. Quan, C.Y. Edosada, M. Mayeda, C. Wiesmann, D. Sutherlin, B.B. Wolf, Bioorg. Med. Chem. Lett. 17, 1438 (2007)

    Article  CAS  PubMed  Google Scholar 

  11. V.J. Reddy, J.S. Chandra, M.V.R. Reddy, Org. Biomol. Chem. 5, 889 (2007)

    Article  CAS  PubMed  Google Scholar 

  12. S.J. Baker, T. Akama, Y.-K. Zhang, V. Sauro, C. Pandit, R. Singh, M. Kully, J. Khan, J.J. Plattner, S.J. Benkovic, V. Lee, K.R. Maples, Bioorg. Med. Chem. Lett. 16, 5963 (2006)

    Article  CAS  PubMed  Google Scholar 

  13. A.K. Malde, S.A. Khedkar, E.C. Coutinho, J. Phys. Org. Chem. 20, 151 (2007)

    Article  CAS  Google Scholar 

  14. J. Adams, Cancer Treat. Rev. 29, 3 (2003)

    Article  CAS  PubMed  Google Scholar 

  15. H.-J. Lenz, Cancer Treat. Rev. 29, 41 (2003)

    Article  CAS  PubMed  Google Scholar 

  16. G.W. Kabalka, B.C. Das, S. Das, Tetrahedron Lett. 42, 7145 (2001)

    Article  CAS  Google Scholar 

  17. A.H. Soloway, W. Tjarks, B.A. Barnum, F.-G. Rong, R.F. Barth, I.M. Codogni, J.G. Wilson, Chem. Rev. 98, 1515 (1998)

    Article  CAS  PubMed  Google Scholar 

  18. J.F. Valliant, K.J. Guenther, A.S. King, P. Morel, P. Schaffer, O.O. Sogbein, K.A. Stephenson, Coord. Chem. Rev. 232, 173 (2002)

    Article  CAS  Google Scholar 

  19. Z. Yinghuai, A.T. Peng, K. Carpenter, J.A. Maguire, N.S. Hosmane, M. Takagaki, J. Am. Chem. Soc. 127, 9875 (2005)

    Article  CAS  PubMed  Google Scholar 

  20. J.-D. Lee, M. Ueno, Y. Miyajima, H. Nakamura, Org. Lett. 9, 323 (2007)

    Article  CAS  PubMed  Google Scholar 

  21. M.-S. Koo, T. Ozawa, R.A. Santos, K.R. Lamborn, A.W. Bollen, D.F. Deen, S.B. Kahl, J. Med. Chem. 50, 820 (2007)

    Article  CAS  PubMed  Google Scholar 

  22. H. Nakamura, M. Ueno, J.-D. Lee, H.S. Ban, E. Justus, P. Fan, D. Gabel, Tetrahedron Lett. 48, 3151 (2007)

    Article  CAS  Google Scholar 

  23. F.L. Rock, W. Mao, A. Yaremchuk, M. Tukalo, T. Crepin, H. Zhou, Y.-K. Zhang, V. Hernandez, T. Akama, S.J. Baker, J.J. Plattner, L. Shapiro, S.A. Martinis, S.J. Benkovic, S. Cusack, M.R.K. Alley, Science 316, 1759 (2007)

    Article  CAS  PubMed  Google Scholar 

  24. C.M. Vogels, L.G. Nikolcheva, D.W. Norman, H.A. Spinney, A. Decken, M.O. Baerlocher, F.J. Baerlocher, S.A. Westcott, Can. J. Chem. 79, 1115 (2001)

    Article  CAS  Google Scholar 

  25. A.M. Irving, C.M. Vogels, L.G. Nikolcheva, J.P. Edwards, X.-F. He, M.G. Hamilton, M.O. Baerlocher, F.J. Baerlocher, A. Decken, S.A. Westcott, New. J. Chem. 27, 1419 (2003)

    Article  CAS  Google Scholar 

  26. J.M. Blacquiere, O. Sicora, C.M. Vogels, M. Čuperlović-Culf, A. Decken, R.J. Ouellette, S.A. Westcott, Can. J. Chem. 83, 2052 (2005)

    Article  CAS  Google Scholar 

  27. T.P. Ribelin, A.S. Judd, I. Akritopoulou-Zanze, R.F. Henry, J.L. Cross, D.N. Whittern, S.W. Djuric, Org. Lett. 9, 5119 (2007)

    Article  CAS  PubMed  Google Scholar 

  28. V.G. Nenajdenko, A.L. Reznichenko, E.S. Balekova. Tetrahedron 63, 3031 (2007)

    Article  CAS  Google Scholar 

  29. C.F. Marcos, S. Marcaccini, G. Menchi, R. Pepino, T. Torroba, Tetrahedron Lett. 49, 149 (2008)

    Article  CAS  Google Scholar 

  30. L. Banfi, A. Basso, V. Cerulli, G. Guanti, R. Riva, J. Org. Chem. 73, 1608 (2008)

    Article  CAS  PubMed  Google Scholar 

  31. L. El Kaim, M. Gizolme, L. Grimaud, J. Oble, J. Org. Chem. 72, 4169 (2007)

    Article  PubMed  Google Scholar 

  32. SAINT 6.02, Bruker AXS, Inc., Madison, Wisconsin, USA. (1997-1999)

  33. G.M. Sheldrick, SADABS, Bruker AXS, Inc., Madison, Wisconsin, USA. (1999)

    Google Scholar 

  34. G.M. Sheldrick, SHELXTL 5.1, Bruker AXS, Inc., Madison, Wisconsin, USA. (1997)

    Google Scholar 

  35. H. Nöth, B. Wrackmeyer, Nuclear magnetic resonance spectroscopy of boron compounds, Springer-Verlag, Berlin, 1978.

    Book  Google Scholar 

  36. T. Beringhelli, G. D’fAlfonso, D. Donghi, D. Maggioni, P. Mercandelli, A. Sironi, Organometallics 23, 5493 (2004)

    Article  CAS  Google Scholar 

  37. K.E. Secor, T.E. Glass, Org. Lett. 6, 3727 (2004)

    Article  CAS  PubMed  Google Scholar 

  38. N. Christinat, R. Scopelliti, K. Severin, Chem. Commun. 1158 (2004)

  39. V. Martichonok, J.B. Jones, J. Am. Chem. Soc. 118, 950 (1996)

    Article  CAS  Google Scholar 

  40. A.J. Blatch, O.V. Chetina, J.A.K. Howard, L.G.F. Patrick, C.A. Smethurst, A. Whiting, Org. Biomol. Chem. 4, 3297 (2006)

    Article  CAS  PubMed  Google Scholar 

  41. R.B. Coapes, F.E.S. Souza, M.A. Fox, A.S. Batsanov, A.E. Goeta, D.S. Yufit, M.A. Leech, J.A.K. Howard, A.J. Scott, W. Clegg, T.B. Marder, J. Chem. Soc., Dalton Trans. 1201 (2001)

  42. L.M. Greig, A.M.Z. Slawin, M.H. Smith, D. Philp, Tetrahedron 63, 2391 (2007)

    Article  CAS  Google Scholar 

  43. P. Rogowska, M.K. Cyrański, A. Sporzyński, A. Ciesielski, Tetrahedron Lett. 47, 1389 (2006)

    Article  CAS  Google Scholar 

  44. M. Dąbrowski, P. Kurach, S. Luliński, J. Serwatowski, J. Appl. Organometal. Chem. 21, 234 (2007)

    Article  Google Scholar 

  45. F. Broccolo, G. Cainelli, G. Caltabiano, C.E.A. Cocuzza, C.G. Fortuna, P. Galletti, D. Giacomini, G. Musumarra, R. Musumeci, A. Quintavalla, J. Med. Chem. 49, 2804 (2006)

    Article  CAS  PubMed  Google Scholar 

  46. J.F. Fisher, S.O. Meroueh, S. Mobashery, Chem. Rev. 105, 395 (2005)

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada

    Francis E. Appoh, Marcy J. Manning, Teri J. Gullon, Margaret A. Hansen, Emily C. Bevans, Krista D. M. Hogan, Courtney S. Turner, Christopher M. Vogels & Stephen A. Westcott

  2. Department of Chemistry, University of New Brunswick, Fredericton, NB E3B 5A3, Canada

    Andreas Decken

Authors
  1. Francis E. Appoh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marcy J. Manning
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Teri J. Gullon
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Margaret A. Hansen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Emily C. Bevans
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Krista D. M. Hogan
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Courtney S. Turner
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Christopher M. Vogels
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Andreas Decken
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Stephen A. Westcott
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Stephen A. Westcott.

About this article

Cite this article

Appoh, F.E., Manning, M.J., Gullon, T.J. et al. Ugi products containing boronate esters. cent.eur.j.chem. 6, 359–364 (2008). https://doi.org/10.2478/s11532-008-0030-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11532-008-0030-7

Key words

Search

Navigation