Efficient and Stereoselective Syntheses of Isomerically Pure 4-Aminotetrahydro-2H-thiopyran 1-Oxide Derivatives
| Autor: | Mitsuhisa Yamano, Ryo Mizojiri, Tatsuya Ito, Kazuaki Takami, Maeda Hiroyuki, Tetsuji Kawamoto |
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| Rok vydání: | 2017 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification Steric effects Thiopyran 010405 organic chemistry Organic Chemistry Sulfoxide 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Proton NMR Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Selectivity Isomerization |
| Zdroj: | Organic Process Research & Development. 21:1034-1041 |
| ISSN: | 1520-586X 1083-6160 |
| DOI: | 10.1021/acs.oprd.7b00147 |
| Popis: | Efficient and stereoselective syntheses of isomerically pure 4-aminotetrahydro-2H-thiopyran 1-oxide derivatives have successfully been achieved. Isomerically pure (4-nitrophenyl)sulfonyltetrahydro-2H-thiopyran 1-oxides were identified by X-ray crystallographic analyses, and isomerically pure sulfoxide derivatives were characterized by 1H NMR. An oxidation reaction of tert-butyl(4-nitrophenyl)sulfonyl(tetrahydro-2H-thiopyran-4-yl)carbamate with Oxone provided steric control, affording its trans sulfoxide with high efficiency and selectivity. From the obtained trans sulfoxide derivatives, cis sulfoxide derivatives were synthesized conveniently by a hydrogen chloride catalyzed isomerization. |
| Databáze: | OpenAIRE |
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