Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition.
作者： Michael P. D’Erasmo , Christine Meck , Chad A. Lewis , Ryan P. Murelli
关键词: Organic chemistry 、 Cycloaddition 、 Chemistry 、 Solvent 、 Dimer 、 Alcohol 、 Combinatorial chemistry 、 Chloroform 、 Bicyclic molecule 、 Tandem 、 Octane
摘要: 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 the reaction require formation methyl triflate-based pre-ylide salt that upon treatment with base in presence alkenes or alkynes leads to α-methoxyenone-containing bicyclic Herein, we describe our discovery use ethanol-stabilized chloroform as solvent generation α-ethoxyenone-containing byproducts. This three-component process was further optimized by gently heating mixture purified version dimer an alcohol prior addition dipolarophile. Using this convenient procedure, several new products can be generated moderate yields. We also highlight method tandem ring-opening/debenzylation α-hydroxytropolones.
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