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Synthesis 2009(13): 2205-2209  
DOI: 10.1055/s-0029-1216816
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of α-Aliphatic and β-Aromatic Substituted Taurines via Regioselective Ring Opening of Thiiranes with Ammonia

Hao Yub, Shengli Caob, Leilei Zhangc, Gang Liuc, Jiaxi Xu*a
a State Key Laboratory of Chemical Engineering Resource, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
Fax: +86(10)64435565; e-Mail: jxxu@mail.buct.edu.cn;
b Department of Chemistry, Capital Normal University, Beijing 100048, P. R. of China
c Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing 100050, P. R. of China
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Publikationsverlauf

Received 30 January 2009
Publikationsdatum:
14. Mai 2009 (online)

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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