Polymer-Supported Stereoselective Synthesis of Benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- benzoxazinothiadiazepinone, bromoketone, cysteine, morpholine, nitrobenzenesulfonyl chloride, serine, solid-phase synthesis, stereoselective synthesis, thiomorpholine, threonine, triethylsilane,
- MeSH
- Alkylation MeSH
- Cyclic S-Oxides chemical synthesis MeSH
- Cyclization MeSH
- Small Molecule Libraries chemical synthesis MeSH
- Polymers chemistry MeSH
- Stereoisomerism MeSH
- Solid-Phase Synthesis Techniques MeSH
- Thiadiazoles chemical synthesis MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Cyclic S-Oxides MeSH
- Small Molecule Libraries MeSH
- Polymers MeSH
- Thiadiazoles MeSH
Herein, we report the stereoselective synthesis of trisubstituted benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides from polymer-supported Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH. After the solid-phase synthesis of N-alkylated-N-sulfonylated intermediates using various 2-nitrobenzenesulfonyl chlorides and bromoketones, the target compounds were obtained via trifluoroacetic acid (TFA)-mediated cleavage from the resin, followed by cyclization of the diazepinone scaffold. Except for the threonine-based intermediates, the inclusion of triethylsilane (TES) in the cleavage cocktail yielded a specific configuration of the newly formed C3 chiral center. The final cyclization resulted in minor or no inversion of the C12a stereocenter configuration.
Department of Organic Chemistry Faculty of Science Palacký University 771 46 Olomouc Czech Republic
JEOL Resonance Inc Musashino 3 1 2 Akishima Tokyo 196 8558 Japan
References provided by Crossref.org
Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine
