Convenient Synthesis of Various Substituted Homotaurines from Alk‐2‐enamides

2013
Various substituted homotaurines(=3-aminopropane-1- sulfonic acids) 6 were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acidto alk-2-enamides 3 (→4), followed by LiAlH4 reduction (→5) and performic acidoxidation (Scheme 1). The configuration of ‘anti’-disubstituted homotaurine‘anti’-6h was deduced from the 3-(acetylthio)alkanamide (=S-(3-amino-1,2-dimethyl-3-oxopropyl) ethanethioate)‘anti’-4h formed in the Michael addition, which was identified via the Karplus equationanalysis, and confirmed by X-ray diffraction analysis. The current route is an efficient method to synthesize diverse substituted homotaurines, including 1-, 2-, and N-monosubstituted, as well as 1,2-, 1,N-, 2,N-, and N,N-disubstituted homotaurines(Table).
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