Tan Yu, Zhao Zhengxing, Chen Zhili, Huang Shengli, Jia Shiqi, Peng Lei, Xu Da, Qin Wenling, Yan Hailong
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P.R. China.
Org Lett. 2020 Jun 5;22(11):4461-4466. doi: 10.1021/acs.orglett.0c01458. Epub 2020 May 11.
An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good to excellent yields. The reaction proceeded under mild conditions using -iodosuccinimide as a promoter, simultaneously constructing one new C-O bond and two new C-C bonds. A tetra-substituted vinylidene -quinone methide intermediate was likely involved, and the steric hindrance of substituents played a critical role in this transformation.
本文报道了一种前所未有的2-炔基萘酚的高非对映选择性二聚反应，以良好至优异的产率提供含有双环[3.2.1]辛烷部分的桥连多环化合物。该反应在温和条件下使用碘代琥珀酰亚胺作为促进剂进行，同时构建一个新的C-O键和两个新的C-C键。可能涉及一个四取代的亚乙烯基-醌甲基化物中间体，并且取代基的空间位阻在该转化中起关键作用。
