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Synthesis 2008(2): 197-200  
DOI: 10.1055/s-2007-1000861
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© Georg Thieme Verlag Stuttgart · New York

Expeditious and Practical Synthesis of Various Substituted Taurines from Amino Alcohols

Wei Zhanga, Boyuan Wanga, Ning Chenb, Da-Ming Dua, Jiaxi Xu*a,b
a Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. of China
b College of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
Fax: +86(10)64435565; e-Mail: jxxu@mail.buct.edu.cn;
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Publication History

Received 3 October 2007
Publication Date:
18 December 2007 (online)

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Abstract

Various substituted taurines have been synthesized expeditiously and practically in satisfactory to good yields directly from amino alcohols using a two-step, one-pot procedure, in which the amino alcohols undergo sulfuric acid esterification and subsequent sodium sulfite substitution. Treatment of amino-substituted secondary alcohols using the same procedure gave 2-substituted or 1,2-di­substituted taurines, indicating the formation of aziridines as intermediates during the substitution step. This method is one of the most efficient routes for preparing structurally diverse 2-substituted and 1,2- and 2,2-disubstituted taurines.

Key words

amino acids - aminoalkanesulfonic acids - amino alcohols - sulfates - taurines