Application of isocyanides derived from α-amino acids as substrates for the Ugi reaction

Synthetic Communications

Volumn 38, Issue 16, 2008, Pages 2714-2721

  Berłozecki, Stanisław ^a   Szymanski, Wiktor ^a   Ostaszewski, Ryszard ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Isocyanides; Racemization; Ugi reaction

Indexed keywords

ALPHA AMINO ACID; CATHEPSIN K INHIBITOR; CYANIDE; DICHLOROMETHANE; ISOCYANIDE; LEWIS ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER;

EID: 49949105650     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802222787     Document Type: Article

References (10)

1. For recent reviews, see (a) Dömling, A.; Ugi, I. "Multcomponent reactions with isocyanides." Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
2. (b) Dömling, A. "Recent developments in isocyanide based multicomponent reactions in applied chemistry." Chem. Rev. 2006, 106, 17-89;
3. (c) Ramon, D. J.; Yus, M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem. Int. Ed. 2005, 44, 1602-1644.
4. (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;
5. (b) Bauer, S. M.; Amstrong, R. Total synthesis of motuporin (Nodularin-V). J. Am. Chem. Soc. 1999, 121, 6355-6366;
6. (c) Bayer, T.; Riemer, C.; Kessler, H. A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid. J. Peptide Sci. 2001, 7, 250.
7. 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.
8. 3 benzamide-containing aminonitriles as potent, selective, orally effective inhibitors of cathepsin K. J. Med. Chem., 2005, 45, 7520-7534.
9. 4-mediated additions of isocyanides to aldehydes and ketones with formation of α-hydroxycarboxylic acid amides. Chem. Ber. 1988, 121, 507-517.
10. 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.