银催化的 3-环丙基丙烯-2-烯-1-酮与氧化吡咯烷酮叶立德的串联环异构化/[5 + 2]环加成反应生成双桥联苯并环庚酮。
Silver-Catalyzed Tandem Cycloisomerization/[5 + 2] Cycloaddition of 3-Cyclopropylideneprop-2-en-1-ones with Oxidopyrylium Ylides to Form Bibridged Benzocycloheptanones.
机构信息
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.
State Key Laboratory, College of Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Weijin Road 94, Tianjin 300071, China.
出版信息
J Org Chem. 2023 Jul 7;88(13):8454-8464. doi: 10.1021/acs.joc.3c00436. Epub 2023 Jun 26.
Herein, we report a mild, one-pot method for silver-catalyzed tandem cycloisomerization/[5 + 2] cycloaddition reactions between readily accessible cyclopropyl-tethered allenyl ketones and benzopyranone-derived oxidopyrylium ylides. The reactions proceed a cyclobutene-fused furan intermediate generated by a cycloisomerization/1,2-carbene transfer/ring-expansion cascade. This method, which features an unprecedented formal [5 + 2] cycloaddition, delivers good to excellent yields of structurally complex bibridged benzocycloheptanones bearing a strained cyclobutane ring and an -bridged ring.
在此，我们报告了一种温和的一锅法，用于银催化的串联环化/[5 + 2]环加成反应，反应底物为易得的环丙基-连接的烯丙基酮和苯并吡喃酮衍生的氧化吡咯烷盐。反应通过环化/1,2-卡宾转移/环扩环级联生成环丁烯稠合的呋喃中间体。该方法具有前所未有的形式[5 + 2]环加成，以良好至优异的收率得到了结构复杂的双桥联苯并环庚酮，其具有刚性的环丁烷环和桥联环。
Zotero 插件