ChemInform Abstract: Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition

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
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