Artículos de revistas
Stereoselective Synthesis Of Azetidine-derived Glutamate And Aspartate Analogues From Chiral Azetidin-3-ones
Registro en:
Tetrahedron. , v. 64, n. 42, p. 9928 - 9936, 2008.
404020
10.1016/j.tet.2008.08.001
2-s2.0-50549094193
Autor
Burtoloso A.C.B.
Correia C.R.D.
Institución
Resumen
The stereoselective syntheses of cis conformationally constrained glutamate and aspartate analogues, containing an azetidine framework were accomplished from (S)-N-tosyl-2-phenylglycine in moderate overall yields. The key steps in these syntheses involved an efficient Wittig olefination of an azetidin-3-one, followed by a highly stereoselective rhodium catalyzed hydrogenation. The route could also be applied to the synthesis of a trans glutamate analogue, since epimerization of cis to trans isomer could be performed using DBU in toluene at reflux. © 2008 Elsevier Ltd. All rights reserved. 64 42 9928 9936 Kanai, Y., Smith, C.P., Hediger, M.A., (1993) Trends Neurosci., 16, p. 365 Szatkowski, M., Attwell, D., (1994) Trends Neurosci., 17, p. 359 Conn, P.J., Patel, J., (1994) The Metabotropic Glutamate Receptors, , Humana, Totowa/New Jersey, NJ pp 1-277 Hollmann, M., Heinemann, S., (1994) Annu. Rev. 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