Data di Pubblicazione:
2004
Citazione:
Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry / C. Pesenti, A. Arnone, P. Arosio, M. Frigerio, S.V. Meille, W. Panzeri, F. Viani, M. Zanda. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 45:26(2004 Jun 21), pp. 5125-5129.
Abstract:
A novel synthesis of enantiopure hydroxyethylamine isosteres 1 has been developed. Reaction of lithiated β-sulfinylethylamines 3 with N-Cbz-imines generated in situ from α-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl 2, that produced the target compounds 1 in very good yields with inversion of configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
peptidomimetics; sulfoxides; Mannich reaction
Elenco autori:
C. Pesenti, A. Arnone, P. Arosio, M. Frigerio, S.V. Meille, W. Panzeri, F. Viani, M. Zanda
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