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
- 1 January 1999
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 149-154
- https://doi.org/10.1039/a808111e
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.Keywords
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