Lu Lin, Huang Haiyang, Yang Shanshan, Bai Jiang, Zhou Yirong, Xiao Qiang
Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Nanchang 330013, China.
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
J Org Chem. 2023 Oct 20;88(20):14435-14444. doi: 10.1021/acs.joc.3c01449. Epub 2023 Sep 28.
A novel palladium-catalyzed intermolecular dearomatization of furans with alkynes via a three-component formal [3 + 2] spiroannulation/allylic substitution cascade reaction has been successfully developed for the stereoselective assembly of spiro 2,5-dihydrofuran frameworks. High step economy and efficacy as well as excellent stereoselectivity were achieved for a broad substrate scope. Two new C-C bonds and one new C-O bond were generated sequentially in a one-pot manipulation. The yielded spiro 2,5-dihydrofuran skeleton bearing a tetrasubstituted carbon center constitutes the core structure for plenty of useful natural products or corresponding analogues. This work represents a significant advancement in the dearomatization strategy for furan heterocycles and provides a practical methodology for expedited access to complex spiro dihydrofuran scaffolds.
通过三组分形式的[3 + 2]螺环化/烯丙基取代级联反应，成功开发了一种新型钯催化的呋喃与炔烃的分子间去芳构化反应，用于立体选择性组装螺环2,5-二氢呋喃骨架。该反应具有高步骤经济性和效率，以及出色的立体选择性，底物范围广泛。通过一锅法操作依次生成了两个新的C-C键和一个新的C-O键。所得到的带有四取代碳中心的螺环2,5-二氢呋喃骨架构成了许多有用天然产物或相应类似物的核心结构。这项工作代表了呋喃杂环去芳构化策略的重大进展，并为快速获得复杂的螺环二氢呋喃支架提供了一种实用方法。
