A stereoselective approach to the synthesis of γ-silylated amino acids

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9545-9548

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

^a CNR   (Italy)

Author keywords

Addition reaction; Amino acids and derivatives; Copper and compounds; Regiocontrol; Silicou and compounds; Stereocontrol

Indexed keywords

AMINO ACID DERIVATIVE; SILICON;

AMINO ACID SYNTHESIS; ARTICLE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032542130     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02120-0     Document Type: Article

References (25)

1. 1. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, N.Y., 1987.
2. 2. Duthaler, R. O. Tetrahedron 1994, 50, 12789.
3. 3. Ohfune, Y. Acc. Chem. Res. 1992, 25, 360.
4. 4. Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
5. 5. William, R. H. The Synthesis of Optically Active α-Amino Acids; Pergamon N.Y.: New York, 1989.
6. 6. Sibi, M. P.; Harris, B. J.; Shay, J. J.: Hajra, S. Tetrahedron 1998, 54, 7221.
7. 7. Tacke, R.; Linoh, H. The Chemistry of Organosilicon Compounds; John Wiley & Sons: New York, 1989.
8. 8. Porter, T. H.; Shive, W. J. Med. Chem. 1968, 11, 402.
9. 9. Walkup, R. D.; Cole, D. C. J. Org. Chem. 1995, 60, 2630.
10. 10. Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277.
11. 11. Smith, R. J.; Bratovanov, S.; Bienz, S. Tetrahedron 1997, 53, 13695.
12. 12. Weidman, B. Chimia 1992, 46, 312.
13. 13. Reginato, G.; Mordini, A.; Caracciolo, M. J. Org. Chem. 1997, 62, 6187.
14. 14. Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Leveque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877.
15. 15. Reginato, G.; Mordini, A.: Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275.
16. 16. Reginato, G.; Mordini, A.; Messina, F.; Degl'Innocenti, A.; Poli, G. Tetrahedron 1996, 52, 10985.
17. 17. Capella, L.; Degl'Innocenti, A.; Reginato, G.; Ricci, A.; Taddei, M. J. Org. Chem. 1989, 54, 1473.
18. 18. Fleming, J. Synthetic Applications of Silylcuprates and Stannylcuprates; Oxford University Press: New York, 1994.
19. 19. Meffre, P.; Gauzy, L.; Branquet, E.; Durand, P.; LeGoffic, F. Tetrahedron 1996, 52, 11215.
20. 20. Posner, B. L.; Flavin, M. J. Biol. Chem. 1972, 56, 4196.
21. 21. Rando, R. R. Acc. Chem. Res. 1975, 8, 281.
22. 22. Castelhano, A. L.; Plivra, D. H.; Taylor, G. J.; Hsieh, K. C.; Krantz, A. J. Am. Chem. Soc. 1984, 106, 2734.
23. 23. Beaulieau, P. L.; Duceppe, J. S.; Johnson, C. J. Org. Chem. 1991, 56, 4196-4204.
24. 1H-NMR δ: 7.53-7.26 [m, 5H], 6.78-6.69 [m, 2H], 5.36-5.24 [m, 1H+1H], 3.73 [s, 3H], 1.44 [s, 9H], 0.34 [s, 6H]. MS m/z 249(1), 234(2), 135(100), 57(29).
25. 25. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.