Synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide

The Mannich-type reaction between alkyl, aryl and heterocyclic aldimines and sulfonium salts for the synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide (NAP-MgO) is described. These products are obtained in moderate to high yields with moderate diastereoselecti...

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Bibliographic Details
Published in:Tetrahedron 2010-07, Vol.66 (27), p.5042-5052
Main Authors: Kantam, M. Lakshmi, Mahendar, Koosam, Sreedhar, Bojja, Choudary, Boyapati. M., Bhargava, Suresh K., Priver, Steven H.
Format: Article
Language:English
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Summary:The Mannich-type reaction between alkyl, aryl and heterocyclic aldimines and sulfonium salts for the synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide (NAP-MgO) is described. These products are obtained in moderate to high yields with moderate diastereoselectivities. The configuration of ethyl-3-{[(4-methylphenyl)sulfonyl]amino}-2-(methylsulfanyl)-3-(4-nitrophenyl)propanoate (major isomer) has been confirmed by X-ray diffraction technique to be anti, and consistent with the assignment based on 1H NMR spectroscopy. These α-sulfanyl-β-amino acid derivatives are important building blocks for pharmaceuticals with potent biological activity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.05.002