Homotaurine and a series of 1-substituted homotaurines were readily synthesized in
satisfactory to good yields via the Michael addition of thioacetic acid to aliphatic
and aromatic α,β-unsaturated nitriles followed by lithium aluminum hydride mediated
reduction and performic acid oxidation. The synthesis of 1,1-disubstituted homotaurines
was attempted with β,β-disubstituted acrylonitriles as starting materials but failed
due to steric hindrance. The current process is an efficient method for the synthesis
of 1-substituted homotaurines.
Key words
acrylonitrile - amino thiols - Michael addition - nucleophile - reduction - oxidation
- thioacetic acid
