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

Authors

  • Zanda Bluke Latvian Institute of Organic Synthesis
  • Meik Sladek Merz Pharmaceuticals GmbH, Eckenheimer Landstrasse 100, Frankfurt am Main 60318
  • Ulrich Abel Merz Pharmaceuticals GmbH, Eckenheimer Landstrasse 100, Frankfurt am Main 60318
  • Valerjans Kauss Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/2193

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

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

Downloads

Published

2015-02-20

Issue

Vol. 51 No. 2 (2015)

Section

Original Papers