Asymmetric synthesis of fluorinated cyclic β-amino acid derivatives through cross metathesis

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4633-4636

  Fustero, Santos ^a,b   Sánchez Roselló, María ^a   Sanz Cervera, Juan F ^a,b   Aceña, José Luis ^b   Del Pozo, Carlos ^a   Fernández, Begoña ^a   Bartolomé, Ana ^a   Asensio, Amparo ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; FLUORINE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; SYNTHESIS;

AMINO ACIDS; CATALYSIS; CYCLIZATION; FLUORINE;

EID: 33750055279     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061892w     Document Type: Article

References (45)

1. (a) Enantioselective Synthesis of β-Amino Acids, 2nd ed.; Juaristi, E. C., Soloshonok, V. A., Eds.: Wiley-VCH Ltd.: New York, 2005.
2. (b) Frackenpohl, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. ChemBioChem 2001, 2, 445-455.
3. (c) Borman, S. Chem. Eng. News 1999, 77, 27.
4. (d) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035.
5. (e) Lelais, G.; Seebach, D. Biopolymers (Pept. Sci.) 2004, 76, 206-243.
6. (f) Seebach, D.; Hook, D. F.; Glättli, A. Biopolymers (Pept. Sci.) 2006, 84, 23-37.
7. (a) Werder, M.; Hauser, H.; Abele, S.; Seebach, D. Helv. Chim. Acta 1999, 82, 1774-1783.
8. (b) Porter, E. A.; Wang, X.; Lee, H.; Weisblum, B.; Gellman, S. H. Nature 2000, 404, 565.
9. (c) Liu, D.; DeGrado, W. F. J. Am. Chem. Soc. 2001, 123, 7553-7559.
10. (d) Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200-12205.
11. (a) Fülöp, F. Chem. Rev. 2001, 101, 2181-2204.
12. (b) Seebach, D.; Kimmerlin, R. S.; Sebesta, R.; Gampo, M. A.; Beck, A. K. Tetrahedron 2004, 60, 7405-7506.
13. (c) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
14. (a) Spatola, A. F. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983.
15. (b) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1994, 59, 649-652.
16. Grubbs, R. H. In Handbook of Metathesis; Wiley-VCH Verlag Gmbh and Co.: KGaA, Weinheim, 2003; Vols. 1-3.
17. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
18. (b) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
19. (c) Jafarpour, L.; Hillier, A. C.; Nolan, S. P. Organometallics 2002, 21, 442-444.
20. (a) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
21. (b) Connon, J. S.; Blechert, S. Angew Chem., Int. Ed. 2003, 42, 1900-1923.
22. (c) Vernall, A. V.; Abell, A. D. Aldrichimica Acta 2003, 36, 93-105.
23. To date, only one example of the synthesis of δ-amino acids through the use of a CM protocol has been described. See: Vasbinder, M. M.; Miller, S. J. J. Org. Chem. 2002, 67, 6240-6242.
24. (a) Perlmutter, P.; Rose, M.; Vounatsos, F. Eur. J. Org. Chem. 2003, 756-760.
25. (b) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253-3265.
26. (c) Gardiner, J.; Anderson, K. H.; Downard, A.; Abell, A. D. J. Org. Chem. 2004, 69, 3375-3382.
27. (d) Abell, A. D.; Gardiner, J. Org. Lett. 2002, 4, 3663-3666.
28. (a) Review: Qiu, X.-L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 6711-6745.
29. (b) Fustero, S.; Pina, B.; Salavert, E.; Navarre, A.; de Arellano, M. C. R.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667-4679.
30. (a) Fustero, S.; Bartolomé, A.; Sanz-Cervera, J. F.; Sánchez-Roselló, M.; García Soler, J.; Ramírez de Arellano, C.; Simón Fuentes, A. Org. Lett. 2003, 5, 2523-2526.
31. (b) Mittendorf, J.; Kunisch, F.; Matzke, M.; Militzer, H.-C.; Schmidt, A.; Schönfeld, W. Bioorg. Med. Chem. Lett. 2003, 13, 433-436.
32. When m = 0 (Scheme 1), competitive side reactions such as isomerization processes of the starting unsaturated esters were observed in our attempts to prepare precursors of RCM 2. In the case of five-membered rings, applying this methodology proved impossible and led mainly to a complex mixture of products: Bartolomé, A. Ph.D. Dissertation, University of Valencia (Spain), 2002.
33. The successful use of fluorinated imidoyl chlorides in CM reactions, which is reported here for the first time, shows once more the versatility of ruthenium catalysts as well as their tolerance for a wide range of functional groups.
34. 2 group may be responsible for the high selectivity observed, also preventing any further isomerization of the double bond. See: Fustero, S.; Sánchez- Roselló, M.; Jiménez, D.; Sanz-Cervera, J. F.; del Pozo, C.; Aceña, J. L. J. Org. Chem. 2006, 71, 2706-2714.
35. (a) Uneyama, K.; Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H. J. Org. Chem. 1993, 58, 32-35.
36. (b) Uneyama, K. J. Fluorine Chem. 1999, 97, 11-25.
37. Lang, R. W.; Greuter, H.; Romann, A. J. Tetrahedron Lett. 1988, 29, 3291-3294.
38. Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry 1997, 8, 3895-3902.
39. Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048-7054.
40. (a) Banik, B. K.; Barakat, K. J.; Wagle, D. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1999, 64, 5746-5753.
41. (b) Kumar, V.; Sharma, A.; Sinha, A. K. Helv. Chim. Acta 2006, 89, 483-495.
42. See compound 11a in ref 11a.
43. Full details of the X-ray structure of cis-(+)-15 will be published in a full account of this work.
44. (a) Oki, T.; Hirano, M.; Tomatsu, K.; Numata, K.; Kamei, H. J. Antibiot. 1989, 42, 1756-1762.
45. (b) Kawabata, K.; Inamoto, Y.; Sakane, K.; Iwamoto, T.; Hashimoto, S. J. Antibiot. 1990, 43, 513-518.