Silylcupration of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4- ethynyloxazolidine: A stereoselective approach to the synthesis of γ- silylated saturated and unsaturated α-amino acids

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9211-9216

  Reginato, Gianna ^a   Mordini, Alessandro ^a   Valacchi, Michela ^a   Grandini, Elena ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYL 3 (TERT BUTOXYCARBONYL) 4 ETHYNYLOXAZOLIDINE; AMINO ACID; DIPEPTIDE; RENIN INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; AMINO ACID SEQUENCE; ARTICLE; ENANTIOMER; HYDROPHOBICITY; OXIDATION; PROTEIN DEGRADATION; SYNTHESIS;

EID: 0032761463     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991272r     Document Type: Article

References (34)

1. Williams, R. M. Synthesis of optically active α-amino acids; Pergamon Press: New York, 1989; Vol. 7.
2. Ohfune, Y. Acc. Chem. Res. 1992, 25, 360.
3. Duthaler, R. O. Tetrahedron 1994, 50, 12789.
4. Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
5. Tacke, R.; Linoh, H. The Chemistry of Organosilicon Compounds; John Wiley & Sons: New York, 1989.
6. Tacke, R. Organosilicon and Bioorganosilicon Chemistry; Structure, Bonding, Reactivity and Synthetic Application; John Wiley & Sons: New York, 1985.
7. Weidman, B. Chimia 1992, 46, 312.
8. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
9. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; John Wiley & Sons: New York, 1987.
10. Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahedron 1998, 54, 7221.
11. Walkup, R. D.; Cole, D. C. J. Org. Chem. 1995, 60, 2630.
12. Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277.
13. Smith, R. J.; Bratovanov, S.; Bienz, S. Tetrahedron 1997, 53, 13695.
14. Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877.
15. Meffre, P.; Gauzy, L.; Branquet, E.; Durand, P.; Goffic, F. L. Tetrahedron 1996, 52, 11215.
16. Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275.
17. Crisp, G. T.; Jiang, Y. L.; Pullman, P. P.; Savi, C. D. Tetrahedron 1997, 53, 17489.
18. Cameron, S.; Khambay, B. P. S. Tetrahedron Lett. 1998, 39, 1987.
19. Reginato, G.; Mordini, A.; Caracciolo, M. J. Org. Chem. 1997, 62, 6187-6192.
20. Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 54, 10227.
21. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
22. Reginato, G.; Mordini, A.; Messina, F.; Degl'Innocenti, A.; Poli, G. Tetrahedron 1996, 52, 10985.
23. Posner, B. L.; Flavin, M. J. Biol. Chem. 1972, 56, 4196.
24. Rando, R. R. Acc. Chem. Res. 1975, 8, 281.
25. Castelhano, A. L.; Plivra, D. H.; Taylor, G. J.; Hsieh, K. C.; Krantz, A. J. Am. Chem. Soc. 1984, 106, 2734.
26. Beaulieau, P. L.; Duceppe, J. S.; Johnson, C. J. Org. Chem. 1991, 56, 4196.
27. Reginato, G.; Mordini, A.; Valacchi, M. Tetrahedron Lett. 1998, 39, 9545.
28. Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317.
29. Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021-4022.
30. Barbero, A.; Cuadrado, P.; Fleming, I.; Gonzales, A. M.; Pulido, F. J.; Sanchez, A. J. Chem. Soc., Perkin Trans. 1 1995, 1525.
31. Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. Tetrahedron Lett. 1998, 39, 5323.
32. Still, W. C.; Ahn, M. K.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
33. Capella, L.; Degl'Innocenti, A.; Reginato, G.; Ricci, A.; Taddei, M. J. Org. Chem. 1989, 54, 1473.
34. Fleming, I. In Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; p 260.