Iodide-Catalyzed Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes

被引：13
作者：
Nambu, Hisanori [1 ]
Onuki, Yuta [1 ]
Ono, Naoki [1 ]
Yakura, Takayuki [1 ]
机构：
[1] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 15期
基金：
日本学术振兴会;
关键词：
iodide catalysts; cyclopropanes; ring opening; cyclization; benzofurans; DONOR-ACCEPTOR CYCLOPROPANES; ONE-POT SYNTHESIS; CYCLOADDITION REACTIONS; CALCIUM IODIDE; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; DERIVATIVES; EXPANSION;
D O I：
10.1002/adsc.201800551
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The ring-opening cyclization of 2',3'-nonsubstituted and 2'-electron-withdrawing group (EWG)-substituted cyclohexane-1,3-dione-2-spirocyclopropanes was accomplished using iodide as a catalyst. The nonsubstituted derivatives afforded 3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in high yields in the presence of trimethylsilyl iodide at room temperature. The EWG-substituted spirocyclopropanes, in turn, underwent regioselective ring opening followed by cyclization, which gave rise to 2-substituted tetrahydrobenzofuran-4-ones when a combination of tetrabutylammonium iodide catalyst and trifluoromethanesulfonic acid was used, whereas calcium iodide afforded the 3-substituted derivatives.
引用
收藏
页码：2938 / 2944
页数：7
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