Issue 2, 1999
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of optically active 3,4,5,6-tetrahydro-2H-1,4-thiazin-3-ones and their benzo analogues by ring transformation of glycidic esters

Karsten Woydowski,   Jörg Fleischhauer,   Jan Schiffer  and  Jürgen Liebscher  

Abstract

Chiral cis and trans glycidic esters 9 substituted by alkyl or ethoxycarbonyl react with cysteamine or o-aminothiophenol 10 by stereoselective ring transformation to non-aromatic optically active 2-(α-hydroxyalkyl)-1,4-thiazin-3-ones 12. The attack of the mercapto function at the α-position of the glycidate occurs predominantly by inversion of configuration. As compared with known reactions of aryl-substituted glycidates with o-aminothiophenol or cysteamine preferentially giving thiazepinones, a remarkable effect of the substituent in the glycidate on the regiochemistry was found.

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Article information

DOI
https://doi.org/10.1039/A808111E
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 149-154

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Synthesis of optically active 3,4,5,6-tetrahydro-2H-1,4-thiazin-3-ones and their benzo analogues by ring transformation of glycidic esters

K. Woydowski, J. Fleischhauer, J. Schiffer and J. Liebscher, J. Chem. Soc., Perkin Trans. 1, 1999, 149 DOI: 10.1039/A808111E

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