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Yang, Li-Cheng; Wang, Ya-Nong; Liu, Ruoyang; Luo, Yixin; Ng, Xiao Qian; Yang, Binmiao; Rong, Zi-Qiang; Lan, Yu; Shao, Zhihui; Zhao, Yu
Nature chemistry, 09/2020, Volume: 12, Issue: 9Journal Article
Medium-sized rings, including those embedded in bridged and fused bicyclic scaffolds, are common core structures of myriad bioactive molecules. Among various synthetic strategies towards their synthesis, intermolecular higher-order cycloaddition provides great potential to build complex medium-sized rings from simple building blocks. Unfortunately, such transformations are often plagued with competitive reaction pathways and low levels of site- and stereoselectivity. Herein, we report catalyst-controlled divergent access to three classes of medium-sized bicyclic compounds in high efficiency and stereoselectivity, by palladium-catalysed cycloadditions of tropones with γ-methylidene-δ-valerolactones. Mechanistic studies and density functional theory calculations disclosed that the divergent reactions stem from the different reaction profiles of the diastereomeric intermediates. While one undergoes either O- or C-allylation to provide 5.5.0 or 4.4.1 bicyclic compounds, the unique conformation of the other diastereomer allows an unconventional alkene isomerization to deliver bridgehead alkene-containing bicyclo4.4.1 compounds. The conversion of these products to diverse complex polycyclic scaffolds has also been demonstrated.
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