Electrochemical ODI-[5+2] Cascade for the Syntheses of Diversely Functionalized Bicyclo[3.2.1]octane Frameworks

• DOI: 10.1021/acs.orglett.1c02321
• Publication Date: 2021-08-17T14:50:12Z
• Authors: Zhaobo Liu; Jialei Hu; Hanfeng Ding
• Keywords: Hypervalent molecule; Natural product; Pinacol

A metal- and hypervalent iodine reagent-free electrochemical oxidative dearomatization-induced [5+2] cycloaddition/pinacol rearrangement cascade reaction was described. The electrosynthetic method showed strong tolerance for vinylphenols, ethynylphenols, allenylphenols, which thus enabled the rapid assembly of diversely functionalized bicyclo[3.2.1]octanes in 41-95% yields up to >20:1 dr. This protocol could be scaled gram amounts should find wide application complex natural product synthesis.