A new strategy for the synthesis of optically pure β-fluoroalkyl β-amino acid derivatives

Organic Letters

Volumn 11, Issue 3, 2009, Pages 641-644

  Fustero, Santos ^a,b   Pozo, Carlos Del ^b   Catalań, Silvia ^b   Alemán, José ^c   Parra, Alejandro ^c   Marcos, Vanesa ^c   Ruano, José Luis García ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^c UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; FLUORINATED HYDROCARBON; SULFOXIDE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, FLUORINATED; STEREOISOMERISM; SULFOXIDES;

EID: 60849109241     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802733t     Document Type: Article

References (47)

1. (a) Seebach, D.; Hook, D. F.; Glättli, A. Biopolymers (Peptide Science) 2006, 84, 23.
2. (b) Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E. C., Soloshonok, V. A., Eds.; Wiley-VCH Ltd.: New York, 2005.
3. (c) Lelais, G.; Seebach, D. Biopolymers (Peptide Science) 2004, 76, 206.
4. (d) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
5. (e) Frackenpohl, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. ChemBioChem 2001, 2, 445.
6. (f) Borman, S. Chem. Eng. News 1999, 77, 27.
7. (a) Seebach, D.; Gardiner, J. Acc. Chem. Res. 2008, 41, 1366-1375.
8. (b) Fülöp, F.; Martikek, T. A.; Tóth, G. K. Chem. Soc. Rev. 2006, 35, 323.
9. (c) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
10. (d) Mathad, R. I.; Gessier, F.; Seebach, D.; Jaun, B. Helv. Chim. Acta 2005, 88, 266.
11. (e) Mathad, R. I.; Jaun, B.; Flögel, O.; Gardiner, J.; Löweneck, M.; Codée, J. D.; Seeberger, P. H.; Seebach, D.; Edmonds, M. K.; Graichen, F. H.; Abell, A. D. Helv. Chim. Acta 2007, 90, 2251.
12. (f) Hook, D. F.; Gessier, F.; Noti, Ch.; Kast, P.; Seebach, D. ChemBioChem 2004, 5, 691.
13. (a) Werder, M.; Hauser, H.; Abele, S.; Seebach, D. Helv. Chim. Acta 1999, 82, 1774.
14. (b) Porter, E. A.; Wang, X.; Lee, H.; Weisblum, B.; Gellman, S. H. Nature 2000, 404, 565.
15. (c) Liu, D.; DeGrado, W. F. J. Am. Chem. Soc. 2001, 123, 7553.
16. (d) Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200.
17. (e) Specker, E.; Bottcher, J.; Lilie, H.; Heine, A.; Schoop, A.; Muller, G.; Griebenow, N.; Klebe, G. Angew. Chem., Int. Ed. 2005, 44, 3140.
18. (f) Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207.
19. (g) Bialy, L.; Waldmann, H. Angew. Chem., Int. Ed. 2005, 44, 2.
20. (h) Isanbor, Ch.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303.
21. (a) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
22. (b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
23. Review: Qiu, X.-L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 6711.
24. F)-AAs, see: (a) Sani, M.; Bruche, L.; Chiva, G.; Fustero, S.; Piera, J.; Volonterio, A.; Zanda, M. Angew. Chem., Int. Ed. 2003, 42, 2060.
25. (b) Fustero, S.; Chiva, G.; Piera, J.; Volonterio, A.; Zanda, M.; Gonzalez, J.; Morán, A. Chem. Eur. J. 2007, 13, 8530.
26. 3(R)-AAs, see:
27. (d) Edmonds, M. K.; Graichen, F. H. N.; Gardiner, J.; Abell, A. D. Org. Lett. 2008, 10, 885.
28. (e) Hook, D. F.; Gessier, F.; Noti, C.; Kast, P.; Seebach, D. ChemBiochem 2004, 5, 691.
29. (f) Sorochinsky, A.; Voloshin, N.; Markovski, A.; Belik, M.; Yasuda, N.; Uekusa, H.; Ono, T.; Bervasov, D. O.; Soloshonok, V. A. J. Org. Chem. 2003, 68, 7448.
30. (g) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461.
31. Jiang, Z.-X.; Qing, F.-L. J. Org. Chem. 2004, 69, 5486, and references therein.
32. For recent reviews of creation of quaternary stereocenters, see: (a) Cozzi, P. G.; Hilfrag, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969.
33. (b) Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473.
34. Soloshonok, V. A.; Soloshonok, I. V.; Kukhar, V. P.; Svedas, V. K. J. Org. Chem. 1998, 63, 1878.
35. Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; de Arellano, M. C. R.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667.
36. Fustero, S.; Jiménez, D.; Sanz-Cervera, J. F.; Sanchez-Roselló, M.; Esteban, E.; Simón-Fuentes, A. Org. Lett. 2005, 7, 3433.
37. (a) García-Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677.
38. (b) García-Ruano, J. L.; Alemán, J. Org. Lett. 2003, 5, 4513.
39. (c) García-Ruano, J. L.; Alemán, J.; Parra, A. J. Am. Chem. Soc. 2005, 127, 13048.
40. García-Ruano, J. L.; Alemán, J.; Alonso, I.; Parra, A.; Marcos, V.; Aguirre, J. Chem. Eur. J. 2007, 13, 6169.
41. García-Ruano, J. L.; Alemán, J.; Catalán, S.; Marcos, V.; Monteagudo, S.; Parra, A.; del Pozo, C.; Fustero, S. Angew. Chem., Int. Ed. 2008, 47, 7941.
42. Only one exception to this general behavior has been observed; see Table 1, entry 8.
43. The absolute configuration of the major diastereoisomers was established by X-ray analysis. See ref 14.
44. The assumption of this structure as the most stable one for the benzyllithium derived from 2b is supported by theoretical calculations. See ref 13.
45. Starting from (R)-sulfoxides, resulting compounds would exhibit an (R)-configuration at this position.
46. Similar approaches were used for explaining the stereochemical results obtained in reactions of sulfinylated thiomethylcarbanions with ketones. See: Arroyo, Y.; Meana, A.; Sanz-Tejedor, M. A.; García-Ruano, J. L. Org. Lett. 2008, 10, 2151.
47. Plietker, B. Synthesis 2005, 2453.