Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry (original) (raw)
A novel synthesis of enantiopure hydroxyethylamine isosteres 1 has been developed. Reaction of lithiated b-sulfinylethylamines 3 with N-Cbz-imines generated in situ from a-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 CH 2 Cl 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.
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