Gao Yanfeng, Wang Hui, Chen Xiaoquan, Qiao Yiyang, Miao Zhiwei
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Weijin Road 94, Tianjin 300071, China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.
J Org Chem. 2023 Aug 18;88(16):11822-11833. doi: 10.1021/acs.joc.3c01114. Epub 2023 Aug 3.
We report a highly efficient and diastereoselective gold and palladium sequential relay catalysis system for the synthesis of furan-fused eight-membered heterocycles. Employing a one-pot procedure, easily accessible enynamides undergo cyclization to generate azadienes in situ, which subsequently participate in diastereoselective formal [4 + 4] cycloadditions with γ-methylene-δ-valerolactones. This strategy enables the rapid and efficient construction of a series of furan-fused azacyclooctanes with diverse substituents in good yields (63-97%) and a high level of diastereoselectivity (7:1 → 20:1 dr).
我们报道了一种用于合成呋喃稠合八元杂环的高效非对映选择性金和钯顺序接力催化体系。采用一锅法，易于获得的烯炔酰胺发生环化反应原位生成氮杂二烯，随后氮杂二烯与γ-亚甲基-δ-戊内酯进行非对映选择性形式上的[4 + 4]环加成反应。该策略能够快速高效地构建一系列具有不同取代基的呋喃稠合氮杂环辛烷，产率良好（63 - 97%）且具有高水平的非对映选择性（7:1 → 20:1 dr）。
