Synthesis, structural characterization and stereocontrolled degradation of 2-azacephams
| Autor: | M. Kovacevic, M. Tomic, Jure J. Herak, Mladen Vinković, I. Lukic, Z. Mandic |
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| Rok vydání: | 1994 |
| Předmět: |
Intramolecular reaction
Bicyclic molecule Chemistry Stereochemistry Organic Chemistry Absolute configuration Regioselectivity Crystal structure Catalysis Inorganic Chemistry chemistry.chemical_compound 4-oxoazetidine-2-sulfinamide 2-azacepham oxide Nucleophile Lactam Stereoselectivity Physical and Theoretical Chemistry |
| Zdroj: | Tetrahedron: Asymmetry. 5:1605-1612 |
| ISSN: | 0957-4166 |
| Popis: | The enantiomerically pure substituted 2-azacephams 5 were synthesized by intramolecular cyclization of sulfinamides 4. Their absolute configurations were confirmed by X-ray crystal structure determination of (5R,6R)-4-benzyl-2-isopropylidene-5-oxo-5-thia-1,4-diazabicyclo[4.2.0]octane-3,8-dione 5a. Nucleophilic opening of 2-azacephams by methanol occurred rapidly to give sulfinates 8 with excellent regio and stereoselectivity. |
| Databáze: | OpenAIRE |
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