Substrate Triggered Stereoselective Preparation of Highly Substituted Organic Carbonates
| Autor: | Laserna, Victor, Martin, Eddy, Escudero-Adán, Eduardo C., Kleij, Arjan W. |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Zdroj: | RECERCAT (Dipòsit de la Recerca de Catalunya) Recercat. Dipósit de la Recerca de Catalunya instname |
| Popis: | Trisubstituted cyclic organic carbonates with multiple though well-defined stereochemical configurations are difficult to prepare. Here we present a conceptual design towards these CO2 based synthons using hydroxyl-substituted cyclic epoxide precursors and their catalytic conversion, to afford these challenging target compounds with fused ring sizes up to eight under excellent stereo-control. The observed stereochemistry of the organic carbonates combined with various control experiments revealed that these compounds are formed through a mechanistic manifold that involves a depolymerization reaction within an oligomeric carbonate induced by a pendent hydroxyl nucleophile. This manifold therefore provides an alternative approach towards CO2 valorization into functional, cyclic carbonate scaffolds of use in synthetic chemistry. |
| Databáze: | OpenAIRE |
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