Application of Isocyanides Derived from α-Amino Acids as Substrates for the Ugi Reaction

REFERENCES

• For recent reviews, see (a) Dömling , A. ; Ugi , I. “Multcomponent reactions with isocyanides.” Angew. Chem. Int. Ed . 2000 , 39 , 3168 – 3210 ; (b) Dömling, A. “Recent developments in isocyanide based multicomponent reactions in applied chemistry.” Chem. Rev. 2006, 106, 17–89; (c) Ramon, D. J.; Yus, M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem. Int. Ed. 2005, 44, 1602–1644 .
   PubMed Web of Science ®Google Scholar
• (a) Behnke , D. ; Taube , R. ; Illgen , K. ; Nerdinger , S. ; Herdweck , E. Substituted 2-(Cyanomethyl-amino)-acetamides by a novel three-component reaction . Synlett. 2004 , 4 , 688 – 692 ; (b) Bauer, S. M.; Amstrong, R. Total synthesis of motuporin (Nodularin-V). J. Am. Chem. Soc. 1999, 121, 6355–6366; (c) Bayer, T.; Riemer, C.; Kessler, H. A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid. J. Peptide Sci. 2001, 7, 250 .
   Google Scholar
• Adang , A. E. ; de Man , A. P. ; Vogel , G. M. ; Grootenhuis , P. D. ; Smit , M. J. ; Peters , C. A. ; Visser , A. ; Rewinkel , J. B. ; van Dinther , T. ; Lucas , H. ; Kelder , J. ; van Aelst , S. ; Meuleman , D. G. ; van Boeckel , C. A. Unique overlap in the prerequisites for thrombin inhibition and oral bioavailability resulting in potent oral antithrombotics . J. Med. Chem. 2002 , 45 , 4419 – 4432 .
   Google Scholar
• Palmer , J. T. ; Bryant , C. ; Wang , D.-X. ; Davis , D. E. ; Setti , E. L. ; Rydzewski , R. M. ; Venkatraman , S. ; Tian , Z.-Q. ; Burrill , L. C. ; Mendonca , R. V. ; Springman , E. ; McCarter , J. ; Chung , T. ; Cheung , H. ; Janc , J. W. ; McGrath , M. ; Somoza , J.R. ; Enriquez , P. Z. ; Yu , W. ; Strickley , R.M. ; Liu , L. ; Venuti , M. C. ; Percival , M. D. ; Falgueyret , J. P. ; Prasit , P. ; Oballa , R. ; Riendeau , D. ; Young , R.N. ; Wesolowski , G. ; Rodan , S. B. ; Johnson , C. ; Kimmel , D. B. ; Rodan, G. Design and synthesis of tri-ring P3 benzamide-containing aminonitriles as potent, selective, orally effective inhibitors of cathepsin K . J. Med. Chem. , 2005 , 45 , 7520 – 7534 .
   Google Scholar
• Seebach , D. ; Adam , G. ; Gees , T. ; Schiess , M. ; Weigand , W. Scope and limitations of the TiCl4-mediated additions of isocyanides to aldehydes and ketones with formation of α-hydroxycarboxylic acid amides . Chem. Ber. 1988 , 121 , 507 – 517 .
   Google Scholar
• Godet , T. ; Bonvin , Y. ; Guillaume , V. ; Merle , D. ; Thozet , A. ; Ciufolini , M. A. Titanium catalysis in the ugi reaction of α-amino acids with aromatic aldehydem . Org. Lett. 2004 , 6 , 3281 – 3284 .
   PubMed Web of Science ®Google Scholar