Liu Xihong, Zhang Jingying, Bai Lutao, Wang Linqing, Yang Dongxu, Wang Rui
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University Lanzhou 730000 China
Chem Sci. 2019 Dec 6;11(3):671-676. doi: 10.1039/c9sc05320d.
A direct catalytic asymmetric multiple dearomatization reaction of phenols was disclosed, which provides expedient access to a series of architecturally complex polycyclic compounds bearing four stereogenic centers in high enantiopurity. The key to achieve such a transformation is the combination of a dearomative 1,8-addition of β-naphthols to -quinone methides generated from propargylic alcohols and a subsequent intramolecular dearomative Diels-Alder reaction. Noteworthily, this protocol enrichs not only the diversity of dearomatized products but also the toolbox of dearomatization strategies.
公开了一种酚类的直接催化不对称多去芳构化反应，该反应能便捷地获得一系列具有四个立体中心且对映体纯度高的结构复杂的多环化合物。实现这种转化的关键是β-萘酚对由炔丙醇生成的醌甲基化物进行去芳构化的1,8-加成反应与随后的分子内去芳构化狄尔斯-阿尔德反应相结合。值得注意的是，该方法不仅丰富了去芳构化产物的多样性，还扩充了去芳构化策略的工具库。
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