Asymmetric addition reactions of lithium (trimethylsilyl)acetylide with chiral r-amino nitrones. synthesis of diastereomerically pure N-hydroxy-r-amino acids

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5627-5630

  Merino, Pedro ^a   Franco, Santiago ^a   Merchan, Francisco L ^a   Tejero, Tomas ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001101886     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9714775     Document Type: Article

References (39)

1. (a) Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 1 (Schreiber, S. L., Ed.), Vol. 2 (Heathcock, C. H., Ed.).
2. (b) Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Houben-Weyl, Thieme: Stuttgart, 1996; Vols. 2 and 3.
3. (a) Carda, M.; Gonzalez, F.; Rodriguez, S.; Marco, J. A. Tetrahedron: Asymmetry 1993, 4, 1799-1802.
4. Ipaktschi, J.; Eckert, T. Chem. Ber. 1995, 128, 1171-1174.
5. Mulzer, J.; Greifenberg, S.; Beckstett, A.; Gottwald, M. Liebigs Ann. Chem. 1992, 1131-1135.
6. Yasuda, M.; Miyai, T.; Shibata, I.; Baba, A.; Nomura, R.; Matsuda, H. Tetrahedron Lett. 1995, 36, 9497-9500.
7. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2814-2820.
8. Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865-5867
9. Herold, P. Helv. Chim. Acta 1988, 71, 354-361.
10. (h) Czernecki S., Franco S., Horns S., Valery. J.-M. Tetrahedron Lett. 1996; 37: 4003-4006.
11. (i) Czernecki S., Horns S., Valery J.-M. J. Org. Chem. 1995; 60: 650-655.
12. (a) Tronchet, J. M. J.; Mihaly, M. E. Helv. Chim. Acta 1972, 55, 1266-1271.
13. (b) Enders, D.; Schankat, J. Helv. Chim. Acta 1995, 78, 970-992.
14. (c) Denis, J.-N.; Tchertchian, S.; Tomassini, A.; Vallee, Y. Tetrahedron Lett. 1997, 38, 5503-5506.
15. (d) Huffman M. A., Yasuda N., DeCamp A. E., Grabowski E. J. J. J. Org. Chem. 1995; 60: 1590-1594.
16. (e) Myers A. G., Tom N. J., Fraley M. E., Cohen S. B., Madar D. J. J. Am. Chem. Soc. 1997; 119: 6072-6094.
17. (f) Osipov, S. N.; Golubev, A. S.; Sewald, N.; Burger, K. Tetrahedron Lett. 1997, 34, 5965-5966.
18. (a) Merino, P.; Anoro, S.; Castillo, E.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1996, 7, 1887-1890.
19. (b) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 3489-3496.
20. (a) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 2381-2401.
21. (b) Merino P., Lanaspa A., Merchan F. L., Tejero T. J. Org. Chem. 1996; 61: 9028-9032.
22. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1997, 38, 1813-1816.
23. For a review see: Ottenheijm, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697-707.
24. (a) Hanessian S., Yang R.-Y. Synlett 1995; 633-634.
25. (b) Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta 1992, 75, 1965-1978.
26. (c) Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 31, 991-994.
27. (d) Murahashi, S.-I.; Shiota, T. Tetrahedron Lett. 1987, 28, 6469-6472.
28. (a) Gouverneur, V.; Lalloz, H. N. Tetrahedron Lett. 1996, 37, 6331-6334.
29. (b) Ohler E., Kanzler S. Phosphorous, Sulfur Silicon 1996; 112: 71-90.
30. (c) Vasella, A.; Huber, R. Helv. Chim. Acta 1987, 70, 1461-1476.
31. Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646.
32. Czernecki, S.; Franco, S.; Valery, J.-M. J. Org. Chem. 1997, 62, 4845-4847.
33. Carlsen, H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
34. Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364
35. See: Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Electronic Conference on Trends in Organometallic Chemistry; Rzepa, H. S., Leach, C., Eds.; Royal Society of Chemistry: London, 1997; Article 003, CD-ROM, ISBN 0-85404-889-8. Internet: http://www.ch.ic.ac.uk/ectoc/ectoc-3/.
36. Merino, P.; Merchan, F. L.; Tejero, T.; Lanaspa, A. Acta Crystallogr. Sect. C 1996, 52, 2536-2538.
37. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450-1456
38. Homologated serines having different functionalities at the R-position are versatile building blocks for asymmetric synthesis. X ) N3: Nitta, H.; Ueda, I.; Hatanaka, M. J. Chem. Soc., Perkin Trans. 1 1997, 1793-1798.
39. X ) OH: Wagner, R.; Tilley, J. W. J. Org. Chem. 1990, 55, 6289-6291. X ) N(OR)R: This work.