Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry |
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Authors: | Cristina Pesenti |
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Affiliation: | CNR--Istituto di Chimica del Riconoscimento Molecolare, sezione `A. Quilico', and Dipartimento di Chimica, Materiali ed Ingegneria Chimica `G. Natta' del Politecnico di Milano, via Mancinelli 7, I-20131 Milano, Italy |
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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. |
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Keywords: | Peptidomimetics Sulfoxides Mannich reaction |
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