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EVALUATION OF AN ENANTIOSELECTIVE SYNTHESIS OF 6-CHLORO-3,4-DIHYDRO-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC ACID 1,1-DIOXIDE AND ITS DERIVATIVES

Zanda Bluke, Meik Sladek, Ulrich Abel, Valerjans Kauss
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Abstract


Step-by-step evaluation of an enantioselective synthesis of (S)- and (R)-ethyl 3,4-dihydro-2H-1,2-benzothiazine-3-carboxylates is
described, starting from (S)- and (R)-methyl 2-acetamido-3-(3-chlorophenyl)propanoates as a source of chirality. A one-pot procedure for transesterification and cleavage of the N-acetyl group was developed to prevent racemization during the hydrolysis of the methyl ester group. It was demonstrated that the synthesized benzothiazines might serve as useful building blocks for enantioselective synthesis of pharmacologically active compounds.

How to Cite
Bluke, Z.; Sladek, M.; Abel, U.; Kauss, V. Chem. Heterocycl. Compd. 2015, 51, 187. [Khim. Geterotsikl. Soedin. 2015, 51, 187.]

For this article in the English edition see DOI 10.1007/s10593-015-1679-4


Keywords


alkyl 2-acetamido-3-phenylacrylate; alkyl 2-acetamido-3-phenylpropanoate; 3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide; asymmetric hydrogenation; enantioselective synthesis; sulfochlorination

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