Artículos de revistas
Chiral Allylsilane Additions To Chiral N-boc-α-amino Aldehydes
Registro en:
Synlett. , v. , n. 1, p. 37 - 40, 2000.
9365214
2-s2.0-0033978057
Autor
Dias L.C.
Meira P.R.R.
Institución
Resumen
Addition of chiral allylsilane 4 to chiral N-Boc-α-amino aldehydes in the presence of SnCl4 in CH2Cl2 at -78 °C affords 1,2-syn homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The diastereoselectivity depends on the aldehyde absolute configuration, with (R)-α-aminoaldehydes (matched case/anti-Felkin addition) exhibiting higher stereoselectivity than its enantiomer (mismatched case/Felkin addition).
1 37 40 Vacca, J.P., Condra, J.H., (1997) Drug Discovery Today, 2, p. 261 Steele, F.R., (1996) Nature Med., 2, p. 257 Rich, D.H., Peptidase inhibitors (1990) Comprehensive Medicinal Chemistry, 2, p. 391. , Sammer, P. G., Ed. Pergamon: Oxford Greenlee, W., (1990) J. Med. Res. Rev., 10, p. 173 Huff, J.R., (1991) J. Med. Chem., 34, p. 2305 Martin, J.A., (1992) Antiviral Res., 17, p. 265 D'Aniello, F., Taddei, M.J., (1992) Org. Chem., 57, p. 5247 D'Aniello, F., Géhanne, S., Taddei, M., (1992) Tetrahedron Lett., 33, p. 5621 D'Aniello, F., Mann, A., Mattii, D., Taddei, M., (1994) J. Org. Chem., 59, p. 3762 Vara Prasad, J.V.N., Rich, D.H., (1991) Tetrahedron Lett., 32, p. 5857 Vara Prasad, J.V.N., Rich, D.H., (1990) Tetrahedron Lett., 31, p. 1803 Dias, L.C., Giacomini, R., (1998) Tetrahedron Lett., 39, p. 5343 Dias, L.C., Giacomini, R., (1998) J. Braz, Chem. Soc., 9, p. 357 Dias, L.C., Meira, P.R.R., Ferreira, E., (1999) Org. Lett., 1, pp. 1335-1338 Fehrentz, J.-A., Castro, B., (1983) Synthesis, 676 Saari, W.S., Fisher, T.E., (1990) Synthesis, p. 453 Ito, A., Takahashi, R., Baba, Y., (1975) Chem Pharm. Bull., 23, p. 3081 Garner, P., Park, J.M., (1987) J. Org. Chem., 52, p. 2361 Jurczak, J., Golebiowski, A., (1989) Chem. Rev., 89, p. 149 Panek, J.S., Liu, P., (1997) Tetrahedron Lett., 38, p. 5127 notenoteEvans, D.A., Coleman, P.J., Dias, L.C., (1997) Angew. Chem., Int. Ed. Engl., 36, p. 2737 Masamune, S., Choy, W., Petersen, J.S., Sita, L.R., (1985) Angew Chem., Int. Ed. Engl., 24, p. 1 Benedetti, F., Miertus, S., Norbedo, S., Tossi, A., Zlatoidzky, P., (1997) J. Org. Chem., 62, p. 9348 Kiyooka, S., Nakano, M., Shiota, F., Fujiyama, R., (1989) J. Org. Chem., 54, p. 5409 Roush, W.R., Palkowitz, A.D., Ando, K., (1990) J. Am. Chem. Soc., 112, p. 6348 note