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

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 via a cyclobutene-fused furan intermediate gen...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 13; pp. 8454 - 8464
Main Authors Huang, Jing, Liang, Yushuang, Sun, Shengnan, Zhang, Ruilong, Miao, Zhiwei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.07.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOBUTANE
APLYDACTONE
C-H
ALKALOIDS
SKELETON
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Summary: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 via a cyclobutene-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 bibridged benzocycloheptanones bearing a strained cyclobutane ring and an O-bridged ring.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00436