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Convenient Synthesis of Various Substituted Homotaurines from Alk‐2‐enamides
Author(s) -
Nai Youfeng,
Xu Jiaxi
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200547
Subject(s) - chemistry , sulfonic acid , reduction (mathematics) , michael reaction , performic acid , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , geometry , mathematics
Various substituted homotaurines (=3‐aminopropane‐1‐sulfonic acids) 6 were readily synthesized in satisfactory to good yields via the Michael addition of thioacetic acid to alk‐2‐enamides 3 (→ 4 ), followed by LiAlH 4 reduction (→ 5 ) and performic acid oxidation ( 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 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 N ‐monosubstituted, as well as 1,2‐, 1, N ‐, 2, N ‐, and N , N ‐disubstituted homotaurines ( Table ).