Iridium-catalyzed ring-opening reactions of unsymmetrical oxabenzonorbornadienes with water and alcohol nucleophiles
| Autor: | Christopher Wicks, Austin Pounder, Jarvis Hill, William Tam |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry education Organic Chemistry Regioselectivity chemistry.chemical_element Alcohol 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Nucleophile Drug Discovery Structural isomer Iridium Alkyl |
| Zdroj: | Tetrahedron Letters. 60:150990 |
| ISSN: | 0040-4039 |
| Popis: | The iridium-catalyzed ring-opening reaction of unsymmetrical oxabenzonorbornadienes (OBD) with water and alcohol nucleophiles is reported, with the effects of various C1-substituents explored. Electron-donating alkyl groups lead entirely to the substituted naphthol derivatives in excellent yields while substitution of the C1 position for electron-withdrawing groups afforded ring-opened products in fair to excellent yields with excellent regioselectivity. The reaction was demonstrated to be highly regioselective for the C2 position with no C3 regioisomer observed in all cases. A proposed mechanism for the formation of C2 regioisomeric ring-opened products has been included. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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