A remarkably simple protocol for the N -formylation of amino acid esters and primary amines

Organic Letters

Volumn 13, Issue 15, 2011, Pages 3952-3955

  Suchý, Mojmír ^a   Elmehriki, Adam A H ^a   Hudson, Robert H E ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID; ESTER; FORMIC ACID; FORMIC ACID DERIVATIVE; IMIDAZOLE; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AMINES; AMINO ACIDS; ESTERS; FORMIC ACIDS; IMIDAZOLES; MOLECULAR STRUCTURE;

EID: 79961050799     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201475j     Document Type: Article

References (32)

1. For the review on acylating agents, see: Olah, G. A.; Ohannesian, L.; Arvanaghi, M. Chem. Rev. 1987, 87, 671 For selected examples of N -formylating agents, see: Martinez, J.; Laur, J. Synthesis 1982, 979
2. Kisfaludy, L.; Ötvös, L., Jr. Synthesis 1987, 510
3. Berry, M. B.; Blagg, J.; Craig, D.; Willis, M. C. Synlett 1992, 659
4. Akikusa, N.; Mitsui, K.; Sakamoto, T.; Kikugawa, Y. Synthesis 1992, 1058
5. Chancellor, T.; Morton, C. Synthesis 1994, 1023
6. Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H. J. Synthesis 1996, 37
7. Giard, T.; Bénard, D.; Plaquevent, J. C. Synthesis 1998, 297
8. Meinnel, T.; Patiny, L.; Ragusa, S.; Blanquet, S. Biochemistry 1999, 38, 4287
9. Yang, D.; Jeon, H. B. Bull. Korean Chem. Soc. 2010, 31, 1424
10. Lei, M.; Ma, L.; Hu, L. Tetrahedron Lett. 2010, 51, 4186
11. For selected examples see: Sheehan, J. C.; Yang, D. D. H. J. Am. Chem. Soc. 1958, 80, 1154
12. Boulay, F.; Tardiff, M.; Brouchon, L.; Vignais, P. Biochem. Biophy. Res. Commun. 1990, 168, 1103
13. Stephenson, K. A.; Zubieta, J.; Banerjee, S. R.; Levadala, M. K.; Taggart, L.; Ryan, L.; McFarlane, N.; Boreham, D. R.; Maresca, K. P.; Babich, J. W.; Valliant, J. F. Bioconjugate Chem. 2004, 15, 128
14. For the recent review on Ugi multicomponent reaction, see: Dömling, A. Chem. Rev. 2006, 106, 17 For selected examples, see: Urban, R.; Marquarding, D.; Seidel, P.; Ugi, I.; Weinelt, A. Chem. Ber. 1976, 110, 2012
15. Mayer, J.; Umkehrer, M.; Kalinski, C.; Ross, G.; Kolb, J.; Burdack, C.; Hiller, W. Tetrahedron Lett. 2005, 46, 7393
16. Jain, R.; Cohen, L. A. Tetrahedron 1996, 52, 5363
17. Guillen, F.; Brégeon, D.; Plaquevent, J. C. Tetrahedron Lett. 2006, 47, 1245
18. We were unable to compare the spectral data obtained for 2a with the literature. There is only one reference describing the use of 2a for the preparation of polymeric polyoxyethylene catalysts, however neither the procedure for the preparation nor the spectral data are provided, see: Topicheva, I. N.; Solovieva, A. B.; Kabanov, V. A. Dokl. Akad. Nauk SSSR 1971, 199, 1084
19. Amere, M.; Lasne, M. C.; Rouden, J. Org. Lett. 2007, 9, 2621
20. Only the optical rotation of unnatural R enantiomer of 2d has been determined, see: Chu, K. S.; Negrete, G. R.; Konopelski, J. P. J. Org. Chem. 1991, 56, 5196
21. Andersen, T. P.; Ghattas, A. B. A. G.; Lawesson, S. O. Tetrahedron 1983, 39, 3419
22. Anderson, W. K.; Bhattacharjee, D.; Houston, D. M. J. Med. Chem. 1989, 32, 119
23. Note that the values for the optical rotation reported for N -formyl Ile-OMe (2i) in Aitali, M.; Allaoud, S.; Karim, A.; Mortreux, A. Tetrahedron: Asymmetry 2000, 11, 1367 and in ref 1h have opposite signs (Table 1). Our value (Table 1) indicates that 2i is dextrorotatory
24. Cappon, J. J.; van der Walle, G. A. M.; Verdegem, P. J. E.; Raap, J.; Lugtenburg, J. Rec. Trav. Chim. Pays-Bas 1992, 111, 517
25. Hinderaker, M. P.; Raines, R. T. Protein Sci. 2003, 12, 1188
26. Jain, R. Org. Prep. Proc. Int. 2001, 33, 405
27. Spectral data of 6a and 6b were in agreement with those previously reported, see: Katritzky, A. R.; Chang, H. X.; Yang, B. Synthesis 1995, 503
28. Kitagawa, T.; Arita, J.; Nagahata, A. Chem. Pharm. Bull. 1994, 42, 1655
29. Kitagawa, T.; Ito, J.; Tsutsui, C. Chem. Pharm. Bull. 1994, 42, 1931. Our attepmts to isolate or detect the presence of N -formyl imidazole in the reaction mixture containing no external nucleophile (1a-1n or 5a, 5b) failed, presumably due to the termal instability of N -formyl imidazole
30. Recently there has been a growing interest in the use of Ugi multicomponent reaction as a key step in the formation of cyclen-derived ligands, suitable for the preparation of, for example, MRI contrast agents, see: Main, M.; Snaith, J. S.; Meloni, M. M.; Jauregui, M.; Sykes, D.; Faulkner, S.; Kenwright, A. M. Chem. Commun. 2008, 5212
31. Piersanti, G.; Remi, F.; Fusi, V.; Formica, M.; Giorgi, L.; Zappia, G. Org. Lett. 2009, 11, 417
32. Tei, L.; Gugliotta, G.; Avedano, S.; Giovenzana, G. B.; Botta, M. Org. Biomol. Chem. 2009, 7, 4406