Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid
| Autor: | Simon N. Kessler, Markus Neuburger, Hermann A. Wegner |
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| Rok vydání: | 2012 |
| Předmět: |
Cyclopropanes
Denticity Molecular Structure 010405 organic chemistry Cyclopropanation Chemistry Electrons General Chemistry Electron 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Catalysis Domino 0104 chemical sciences Lewis acid catalysis Alkadienes Pyridazines Colloid and Surface Chemistry Organic chemistry Molecule Lewis acids and bases Lewis Acids |
| Zdroj: | Journal of the American Chemical Society |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja308858y |
| Popis: | A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations. |
| Databáze: | OpenAIRE |
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