Synthesis of Polyfunctionalized Bicyclo[5.3.1]undecadiene Ring Systems Using a Two-Carbon Ring-Expansion of Cyclobutene Intermediates
| Autor: | Michel Miesch, Gaëtan L.A. Mislin |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Dimethyl acetylenedicarboxylate Bicyclic molecule Cyclobutene Organic Chemistry Silyl enol ether Ring (chemistry) Medicinal chemistry Cycloaddition chemistry.chemical_compound Alicyclic compound chemistry Electrophile Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | European Journal of Organic Chemistry. 2001:1753-1759 |
| ISSN: | 1099-0690 1434-193X |
| DOI: | 10.1002/1099-0690(200105)2001:9<1753::aid-ejoc1753>3.0.co;2-e |
| Popis: | The ZrCl4-catalyzed [2+2] cycloaddition of the silyl enol ether derived from monoprotected bicyclo[3.3.1]nonane-2,6-dione 7 with ethyl propynoate led after acidic treatment to the cyclobutene derivative 12. Treatment of the latter with HBF4 in refluxing ethanol smoothly afforded the two-carbon ring-expansion product 13. On the other hand, the enolate of the β-oxobicyclo[3.3.1]nonane ester 14 has been found to react with electrophilic acetylenes [ethyl propynoate, dimethyl acetylenedicarboxylate (DMAD)] to afford bicyclo[5.3.1]undecadiene derivatives 15, 16, most probably through the intermediacy of a tricyclo[5.3.1.02,5]undecene ring system. |
| Databáze: | OpenAIRE |
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