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

页码：8454 / 8464

页数：11

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