Straightforward synthesis of chiral silylated amino acids through hydrosilylation

European Journal of Organic Chemistry

Volumn , Issue 18, 2008, Pages 3107-3112

  Marchand, Damien ^a,b   Martinez, Jean ^a,b   Cavelier, Florine ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b CISTIM   (Belgium)

Author keywords

Amino acids; Hydrosilylation; Peptide analogues; Peptides

Indexed keywords

EID: 53749094171     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800066     Document Type: Article

References (40)

1. G. A. Showell, J. S. Mills, Drug Discovery Today 2003, 8, 551-556.
2. W. Bains, R. Tacke, Curr. Opin. Drug Discovery Development 2003, 6, 526-543.
3. H. Ishikawa, H. Yamanaka, T. Kawamoto, A. Tanaka, Applied Microbiol. Biotechnol. 1999, 53, 19-22.
4. F. Cavelier, B. Vivet, J. Martinez, A. Aubry, C. Didierjean, A. Vicherat, M. Marraud, J. Am. Chem. Soc. 2002, 124, 2917-2923.
5. F. Cavelier, D. Marchand, J. Martinez, S. Sagan, J. Pept. Res. 2004, 63, 290-296.
6. T. H. Porter, W. Shive, J. Med. Chem. 1968, 11, 402-415.
7. B. Weidmann, Chimia 1992, 46, 312-313.
8. R. Fitzi, D. Seebach, Tetrahedron 1988, 44, 5277-5292.
9. R. D. Walkup, D. C. Cole, B. R. Whittlesey, J. Org. Chem. 1995, 60, 2630-2634.
10. H. Yamanaka, T. Fukui, T. Kawamoto, A. Tanaka, Appl. Microbiol. Biotechnol. 1996, 45, 51-55.
11. M. Pietzsch, T. Waniek, R. J. Smith, S. Bratovanov, S. Bienz, C. Syldatk, Monatshefte Chem. 2000, 131, 645-653.
12. J.-X. Chen, J. A. Tunge, J. R. Norton, J. Org. Chem. 2002, 67, 4366-4369.
13. R. J. Smith, S. Bratovanov, S. Bienz, Tetrahedron 1997, 53, 13695-13702.
14. R. Tacke, M. Merget, R. Bertermann, M. Bernd, T. Beckers, T. Reissmann, Organometallics 2000, 19, 3486-3497.
15. B. Vivet, F. Cavelier, J. Martinez, Eur. J. Org. Chem. 2000, 807-811.
16. B. Vivet, F. Cavelier, J. Martinez, C. Didierjean, M. Marraud, A. Aubry, Acta Crystallogr., Sect. C 2000, 56, 1452-1454.
17. G. Reginato, A. Mordini, M. Valacchi, Tetrahedron Lett. 1998, 39, 9545-9548.
18. G. Reginato, A. Mordini, M. Valacchi, E. Grandini, J. Org. Chem. 1999, 64, 9211-9216.
19. C. Bolm, A. Kasyan, K. Drauz, K. Gunther, G. Raabe, Angew. Chem. Int. Ed. 2000, 39, 2288-2290.
20. G. D. Liu, S. M. Sieburth, Org. Lett. 2003, 5, 4677-4679.
21. M. Merget, K. Gunther, M. Bernd, E. Gunther, R. Tacke, J. Organomet. Chem. 2001, 628, 183-194.
22. R. Tacke, V. I. Handmann, Organometallics 2002, 21, 2619-2626.
23. R. J. Smith, S. Bienz, Helv. Chim. Acta 2004, 87, 1681-1696.
24. I. Ojima, The Chemistry of Organic Silicon Compounds, John Wiley & Sons, New York, 1989, pp. 1479-1526.
25. I. Ojima, Catalytic Asymmetric Synthesis, VCH, New York, 1993.
26. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
27. J. Thibon, L. Latxague, G. Déléris, J. Org. Chem. 1997, 62, 4635-4642.
28. M. L. Miller, R. West, Chem. Commun. 1999, 1797-1798.
29. M. Igarashi, T. Fuchikami, Tetrahedron Lett. 2001, 42, 1945-1947.
30. M. Itazaki, Y. Nishihara, K. Osakada, J. Org. Chem. 2002, 67, 6889-6895.
31. N. Duffaut, P. Bourgeois, J. Dunoguès, R. Calas, J. Organomet. Chem. 1972, 46, 41-44.
32. P. A. Lander, L. S. Hegedus, J. Am. Chem. Soc. 1994, 116, 8126-8132.
33. X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, R. A. Widenhoefer, J. Org. Chem. 2002, 67, 2778-2788.
34. I. Ojima, K. Hirai, Asymetric Synthesis, Academic, New York 1985, vol. 5, pp. 103-146.
35. C. Douat, A. Heitz, J. Martinez, J. A. Fehrentz, Tetrahedron Lett. 2001, 42, 3319-3321.
36. M. Carrasco, R. J. Jones, S. Kamel, H. Rapoport, T. Truong, Org. Synth. 1992, 70, 29-34.
37. J. L. Speier, Advances in Organometallic Chemistry, Academic, New York, 1979, vol. 17, pp. 407-447.
38. D. A. de Vekki, V. N. Spevak, E. A. Kuchaev, N. K. Skvortsov, Russ. J. Gen. Chem. 2005, 75, 1757-1762.
39. A. Hamze, O. Provot, M. Alami, J. D. Brion, Org. Lett. 2005, 7, 5625-5628.
40. N. Sabourault, G. Mignani, A. Wagner, C. Mioskowski, Org. Lett. 2002, 4, 2117-2119.