2-Vinyl Threoninol Derivatives via Acid-Catalyzed Allylic Substitution of Bisimidates
| Autor: | Varun Kumar, Aigars Jirgensons, Dace Rasina, Kristine Klimovica |
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| Rok vydání: | 2015 |
| Předmět: |
Allylic rearrangement
Vinyl Compounds Molecular Structure 2-vinyl threoninol Stereochemistry Chemistry Organic Chemistry Stereoisomerism Bond formation Amino Alcohols Stereocenter Allyl Compounds Carbenium ion chemistry.chemical_compound Cyclization Acid catalyzed Imidoesters Stereoselectivity Threonine Butylene Glycols Oxazoles |
| Zdroj: | The Journal of Organic Chemistry. 80:5934-5943 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.5b00529 |
| Popis: | A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C-N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds. |
| Databáze: | OpenAIRE |
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