| Autor: |
Michael P. D'Erasmo, Ryan P. Murelli, Christine Meck, Chad A. Lewis |
| Rok vydání: |
2016 |
| Předmět: |
|
| Zdroj: |
ChemInform. 47 |
| ISSN: |
0931-7597 |
| DOI: |
10.1002/chin.201638116 |
| Popis: |
α-Hydroxy-γ-pyrone-based oxidopyrylium cycloaddition reactions are useful methods for accessing a highly diverse range of oxabicyclo[3.2.1]octane products. Intermolecular variants of the reaction require the formation of a methyl triflate-based pre-ylide salt that upon treatment with base in the presence of alkenes or alkynes leads to α-methoxyenone-containing bicyclic products. Herein, we describe our discovery that the use of ethanol-stabilized chloroform as solvent leads to the generation of α-ethoxyenone-containing bicyclic byproducts. This three-component process was further optimized by gently heating a mixture of a purified version of the oxidopyrylium dimer in the presence of an alcohol prior to addition of a dipolarophile. Using this convenient procedure, several new oxidopyrylium cycloaddition products can be generated in moderate yields. We also highlight the method in a tandem ring-opening/debenzylation method for the generation of α-hydroxytropolones. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
|
Plný text