A novel stereoselective [8+2] double cycloaddition route to hydronaphthalene ring systems

作者：Ying Weijiang; Zhang Lei; Wiget Paul A; Herndon James W^*

来源：Tetrahedron Letters, 2016, 57(27-28): 2954-2956.

DOI：10.1016/j.tetlet.2016.05.059

• Cycloaddition
• Electrocyclic ring closure
• Rearrangement

Substituted hydronaphthalenes where each of the ten carbons of the two-ring system contains a functionality were obtained through a tandem [8+2] cycloaddition and base-catalyzed rearrangement process using dienylfurans and electron-deficient alkynes. If the [8+2] process is conducted under solvent-free conditions the process could be conducted in a single reaction flask without isolation of the chromatographically sensitive [8+2] cycloadducts. A mechanism involving base catalyzed alkene positional isomerization followed by disrotatory electrocyclic ring closure was proposed for the key reaction step that converts [8+2] cycloadducts to hydronaphthalenes. The products undergo selective ring opening-isomerization processes upon treatment with Lewis acids.

• 出版日期2016-7-6