Evaluation of an Enantioselective Synthesis of 6-Chloro-3,4-Dihydro-2H-1,2-Benzothiazine-3-Carboxylic Acid 1,1-Dioxide and Its Derivatives

Chemistry of Heterocyclic Compounds 2015
Zanda Bluķe, Meik Sladek, Ulrich Abel, Valerjans Kauss

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.

Keywords
3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide, alkyl 2-acetamido-3-phenylacrylate, alkyl 2-acetamido-3-phenylpropanoate, asymmetric hydrogenation, enantioselective synthesis, sulfochlorination
DOI
10.1007/s10593-015-1679-4
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-015-1679-4

Bluķe, Z., Sladek, M., Abel, U., Kauss, V. Evaluation of an Enantioselective Synthesis of 6-Chloro-3,4-Dihydro-2H-1,2-Benzothiazine-3-Carboxylic Acid 1,1-Dioxide and Its Derivatives. Chemistry of Heterocyclic Compounds, 2015, Vol.51, Iss.2, pp.187-193. ISSN 0009-3122. Available from: doi:10.1007/s10593-015-1679-4

Publication language
English (en)