Convenient Synthesis of Various Substituted Homotaurines from Alk‐2‐enamides. Issue 7 (12th July 2013)

• Record Type: Journal Article
• Authors: Nai, Youfeng; Xu, Jiaxi
• Is Part Of: Helvetica chimica acta. Volume 96:Issue 7(2013:Jul.)
• Page Start: 1355
• Page End: 1365
• Publication Date: 2013-07-12
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201200547
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Various substituted homotaurines (=3‐aminopropane‐1‐sulfonic acids) <bold>6</bold> were readily synthesized in satisfactory to good yields <italic>via</italic> the <italic>Michael</italic> addition of thioacetic acid to alk‐2‐enamides <bold>3</bold> (→<bold>4</bold>), followed by LiAlH₄ reduction (→<bold>5</bold>) and performic acid oxidation (<italic>Scheme 1</italic>). The configuration of '<italic>anti'</italic>‐disubstituted homotaurine '<italic>anti</italic>'‐<bold>6h</bold> was deduced from the 3‐(acetylthio)alkanamide (=<italic>S‐</italic>(3‐amino‐1, 2‐dimethyl‐3‐oxopropyl) ethanethioate)'<italic>anti</italic>'‐<bold>4h</bold> formed in the <italic>Michael</italic> addition, which was identified <italic>via</italic> the <italic>Karplus</italic> equation analysis, and confirmed by X‐ray diffraction analysis. The current route is an efficient method to synthesize diverse substituted homotaurines, including 1‐, 2‐, and <italic>N</italic>‐monosubstituted, as well as 1, 2‐, 1, <italic>N</italic>‐, 2, <italic>N</italic>‐, and <italic>N</italic>, <italic>N</italic>‐disubstituted homotaurines (<italic>Table</italic>).</p> </abstract>