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DOI: 10.1055/s-0029-1216816
Synthesis of α-Aliphatic and β-Aromatic Substituted Taurines via Regioselective Ring Opening of Thiiranes with Ammonia
Publication History
Publication Date:
14 May 2009 (online)
Abstract
Thiiranes are important starting materials for the synthesis of substituted taurines. The regioselectivity of ring-opening reactions of thiiranes with ammonia in the presence of silver nitrate was investigated. The results of the ring-opening reaction and subsequent peroxy acid oxidation indicate that alkyl-substituted thiiranes give rise to 1-monoalkyl- and 1,1-dialkyltaurines, whereas aryl-substituted thiiranes produce 2-aryl-, 2-alkyl-2-aryl-, and 2,2-diaryltaurines. This shows that alkyl-substituted thiiranes were attacked on their less-substituted ring carbon atoms, while aryl-substituted thiiranes were attacked on their more substituted ring carbon atoms. The current method is an effective and atom-economic route for the synthesis of mono- and disubstituted α-alkyl- and β-aryl-substituted taurines.
Key words
amino acid - aminoalkanesulfonic acid - regioselectivity - ring-opening reaction - synthesis - thiirane - taurine
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