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

Kantam, M. Lakshmi ; Mahendar, Koosam ; Sreedhar, Bojja ; Choudary, Boyapati. M. ; Bhargava, Suresh K. ; Priver, Steven H. (2010) Synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide Tetrahedron, 66 (27-28). pp. 5042-5052. ISSN 00404020

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Official URL: http://doi.org/10.1016/j.tet.2010.05.002

Related URL: http://dx.doi.org/10.1016/j.tet.2010.05.002

Abstract

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.

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ID Code:131660
Deposited On:07 Dec 2022 10:46
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