A convenient conversion of α-aminoacids into NH-Boc protected α-aminoketones via imidazolides

Synlett

Volumn , Issue 9, 1998, Pages 1013-1015

  Bonini, Bianca F ^a   Comes Franchini, Mauro ^a   Fochi, Mariafrancesca ^a   Mazzanti, Germana ^a   Ricci, Alfredo ^a   Varchi, Greta ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001511789     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1831     Document Type: Article

References (37)

1. a) Angle, S. R.; Boyle, J. P. Tetrahedron Lett. 1995, 36, 6185.
2. b) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721.
3. c) Wesson, B. K.; Gibson, W. K.; Stuart, R. S.; Williams, H. W. R.; Yates, C. H. J. Med. Chem. 1972, 15, 651.
4. d) Marrow, D. F.; Johnson, P. C.; Tonabi, H.; Williams, D.; Wedding, D. L.; Craig, J. W.; Majewski, R. F.; Braselton, J. P.; Gallo, D. G. J. Med. Chem. 1973, 16, 736.
5. a) Tramontini, M. Synthesis 1982, 605.
6. b) Reetz, M. T.; Angew. Chem. Int. Ed. Engl. 1991, 30, 1531.
7. Mayer, D. in Houben-Weyl, Methoden der Organischen Chemie, 4th Edit., E. Müller Ed., Vol. 7, 2c Thieme Verlag, Stuttgart, 1977, pp 2253.
8. b) Fischer, L. E.; Muchowski, J. M.; Org. Prep. Proced. Int. 1990, 22, 399.
9. c) Pace, R. D.; Kabalka, G. W. J. Org. Chem. 1995, 60, 4838.
10. a) Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866.
11. b) Klix, R. C.; Chamberlin, S. A.; Bhatia, A. V.; Davis, D. A.; Hayes, T. K.; Rojos, F. G.; Koops, R. W. Tetrahedron Lett. 1995, 36, 1791.
12. c) Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157.
13. d) Knudsen, C. G.; Rapoport, H. J. Org. Chem. 1983, 48, 2260.
14. Palev, M. R.; Sardina, F. J. Tetrahedron Lett. 1996, 37, 3403.
15. Reetz, M. T.; Drawes, M. W.; Lannick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asym. 1990, 6, 375.
16. Jennings-White, C.; Almquist, R. G. Tetrahedron Lett. 1982, 23, 2533.
17. a) Chen, P.; Cheng, P. T. W.; Spergel, S. H.; Zahler, R.; Wang, Z.; Thottathil, J.; Barrish, J. C.; Polniaszek, R. P. Tetrahedron Lett. 1997, 38, 3175.
18. b) Gramble, M. P.; Giblin, G. M.; Montana, J. G.; O'Brien, P.; Ockendon, T. P.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7457.
19. c) Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999.
20. d) Dufour, M. N.; Jauin, P.; Poncet, J.; Pantaloni, A.; Castro, B. J. Chem. Soc. Perkin Trans. I 1986, 1895.
21. e) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727.
22. McClure, D. E.; Arison, B. H.; Jones, J. H.; Baldwin, J. A. J. Org. Chem. 1981, 46, 2433.
23. Kocienski, P. J. in Protecting Groups, Georg Thieme Verlag, Stuttgart-New York 1994.
24. a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 39, 3815.
25. b) Levin, I. J.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
26. Anderson, G. W.; Paul, R. J. Org. Chem. 1962, 27, 2094.
27. Anderson, G. W.; Paul, R. J. Am. Chem. Soc. 1960, 82, 4596.
28. Staab, H. A.; Jost, E. Liebigs Ann. Chem. 1962, 655, 90.
29. Mitchell, R. H.; Iyer, V. S. Tetrahedron Lett. 1993, 34, 3683.
30. Nimitz, J. S.; Mosher, H. S. J. Org. Chem. 1981, 46, 211.
31. Bhattacharya, A.; Williams, J. M.; Amato, J. S.; Dolling, U. H.; Grabowski, E. J. J. Synth. Commun. 1990, 2683.
32. Two equivalents of Grignard reagent were used on the assumption of proton abstraction from the carbamate.
33. Typical procedure for the synthesis of α-amino ketones
34. Buchi, G.; Wuest, H. J. Org. Chem. 1969, 34, 1122.
35. Swarin, M.; Neumann, W. L. Tetrahedron Lett. 1987, 28, 3217.
36. Choi, S.-K.; Lee, J.-S.; Kim, J.-H.; Lee, W. K. J. Org. Chem. 1997, 62, 743 and references cited therein.
37. 11MgBr in the presence of CuI (6% mol), led after 48 h at rt to 15% of 7 and to recovery of about 80% of the starting amide.