First highly diastereoselective synthesis of syn α-methyl β-fluoroalkyl β-amino esters

Organic Letters

Volumn 1, Issue 7, 1999, Pages 977-980

  Fustero, Santos ^a   Pina, Belén ^a   García De La Torre, Marta ^a   Navarro, Antonio ^a   Ramirez De Arellano, Carmen ^a   Simón, Antonio ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000494347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990774o     Document Type: Article

References (45)

1. Reviews: (a) Cole, D. Tetrahedron 1994, 50, 9517.
2. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3.
3. (c) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117.
4. (d) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
5. (a) Pettit, G. R.; Kamano, Y.; Kizu, H.; Dufresne, C.; Herald, C. L.; Bontems, R. J.; Schmidt, J. M.; Boettner, F. E.; Nieman, R. A. Heterocycles 1989, 28, 553.
6. (b) Carter, D. C.; Moore, E. R.; Mynderse, J. S.; Niemczura, W. P.; Todd, J. S. J. Org. Chem. 1984, 49, 236.
7. (c) Fernández, R.; Rodríguez, J.; Quiñoa, E.; Riguera, R.; Muñoz, L.; Fernández-Suarez, M.; Debitus, C. J. Am. Chem. Soc. 1996, 118, 11635.
8. (d) Hu, T.; Panek, J. J. J. Org. Chem. 1999, 64, 3000.
9. See for example: (a) Seebach, D.; Estermann, H. Tetrahedron Lett. 1987, 28, 3103.
10. (b) Juaristi, E.; Escalante, J. J. Org. Chem. 1993, 58, 2282 and literature cited therein.
11. (c) Braschi, I.; Cardillo, J.; Tomasini, C.; Venezia, R. J. Org. Chem. 1994, 59, 7792.
12. (d) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455.
13. (e) Sewald, N.; Hiller, K.; Körner, H.; Findeisen, M. J. Org. Chem. 1998, 63, 7263.
14. (a) Davies, S. G.; Fenwick, D. R. J. Chem. Soc., Chem. Commun. 1995, 1109.
15. (b) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1994, 59, 649.
16. (c) Enders, D.; Bettray, W.; Raabe, G.; Runsik, J. Synthesis 1994, 1322.
17. Cardillo, G.; Tolomelli, A.; Tomasini, C. J. Org. Chem. 1996, 61, 8651.
18. (a) Bartoli, G.; Cimarelli, C.; Marcantoni, E.; Palmieri, G.; Petrini, M. J. Org. Chem. 1994, 59, 5328.
19. (b) Palmieri, G.; Cimarelli, C. J. Org. Chem. 1996, 61, 5557.
20. (a) David, O.; Blot, J.; Bellec, Ch.; Fargeau-Bellasoued, M. C.; Haviari, G.; Célérier, J. P.; Lhommet, G.; Gramain, J. C.; Gardette, D. J. Org. Chem. 1999, 64, 3122.
21. (b) See also: Folmer, J. J.; Acero, C.; Thai, D. L.; Rapoport, H. J. Org. Chem. 1998, 63, 8170.
22. (c) For asymmetric hydrogenation of α-unsubstituted β-enamino acid derivatives, see: Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
23. (a) Banks, R. E.; Tatlow, J. C.; Smart, B. E. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
24. (b) Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991.
25. (c) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry, Wiley: Chichester, U.K., 1991.
26. (d) German, L.; Zemskov, S. New Fluorinating Agents in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, Germany, 1989.
27. (a) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Biomedical Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1993.
28. (b) Ojima, I.; McCarthy, J. R.; Welch, J. T. Biomedical Frontiers of Fluorine Chemistry; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996.
29. (c) Urban, J. J.; von Tersch, R. L. J. Org. Chem. 1999, 64, 3409 and literature cited therein.
30. (a) Fustero, S.; Navarro, A.; Diaz, D.; de la Torre, M. G.; Asensio, A.; Sanz, F.; Liu González, M. J. Org. Chem. 1996, 61, 8849.
31. (b) Fustero, S.; Navarro, A.; Asensio, A. Tetrahedron Lett. 1997, 38, 4891. Corrigenda: Tetrahedron Lett. 1997, 38, 6477.
32. (b) Fustero, S.; Navarro, A.; Asensio, A. Tetrahedron Lett. 1997, 38, 4891. Corrigenda: Tetrahedron Lett. 1997, 38, 6477.
33. (c) Fustero, S.; Navarro, A.; Pina, B.; Asensio, A.; Bravo, P.; Crucianelli, M.; Volonterio, A.; Zanda, M. J. Org. Chem. 1998, 63, 6210.
34. Fustero, S.; Pina, B.; Simon Fuentes, A. Tetrahedron Lett. 1997, 38, 6771.
35. Several fluorine-containing amino acids have been used in the design of protease and suicide inhibitors. See for example: Fluorine-containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, U.K., 1994.
36. Kaneko, S.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 1993, 58, 2302.
37. Abouabdellah, A.; Bégué, J.-P.; Bonnet-Delpon, D.; Thanh Nga, T. T. J. Org. Chem. 1997, 62, 8826 and literature cited therein.
38. Uneyama, K.; Hao, J.; Amii, H. Tetrahedron Lett. 1998, 39, 4079.
39. (a) Soloshonok, V. A.; Soloshonok, I. V.; Kukhar, V. P.; Svedas, V. K. J. Org. Chem. 1998, 63, 1878 and literature cited therein. For the biocatalytic and enantioselective biomimetic version with α-unsubstituted β-fluoroalkyl β-amino acids, see:
40. (b) Soloshonok, V. A.; Soloshonok, I. V.; Ono, T. J. Org. Chem. 1997, 62, 7538 and literature cited therein.
41. Uneyama, K.; Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H. J. Org. Chem. 1993, 58, 32.
42. 2O) or tetrahydrofuran (THF) gave poorer results.
43. 3; C, 55.08; H, 5.94; N, 4.59. Found: C, 55.10; H, 5.96; N, 4.57.
44. 2O (1:1) as the solvent afforded to (2R*,3R*)-6 in 90% overall yield: (matrix presented)
45. Full details of the X-ray structure of (2R*,3R*)-5a will be published in a full account of this work.