Author/Authors :
Pesenti، نويسنده , , Cristina and Arnone، نويسنده , , Alberto and Arosio، نويسنده , , Paolo and Frigerio، نويسنده , , Massimo and Meille، نويسنده , , Stefano V. and Panzeri، نويسنده , , Walter and Viani، نويسنده , , Fiorenza and Zanda، نويسنده , , Matteo، نويسنده ,
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 CH2Cl2, 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.
