Silver-Catalyzed Tandem Cycloisomerization/[5+2] Cycloaddition of 3-Cyclopropylideneprop-2-en-1-ones with Oxidopyrylium Ylides to Form Bibridged Benzocycloheptanones

被引：1
|
作者：
Huang, Jing [1 ]
Liang, Yushuang [1 ]
Sun, Shengnan [1 ]
Zhang, Ruilong [1 ]
Miao, Zhiwei [1 ,2 ]
机构：
[1] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期
关键词：
C-H; CYCLOBUTANE; APLYDACTONE; ALKALOIDS; SKELETON;
D O I：
10.1021/acs.joc.3c00436
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a mild, one-potmethod for silver-catalyzedtandemcycloisomerization/[5 + 2] cycloaddition reactions between readilyaccessible cyclopropyl-tethered allenyl ketones and benzopyranone-derivedoxidopyrylium ylides. The reactions proceed via acyclobutene-fused furan intermediate generated in situ 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 bibridgedbenzocycloheptanones bearing a strained cyclobutane ring and an O-bridged ring.
引用
收藏
页码：8454 / 8464
页数：11
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