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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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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Abstract 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.
AbstractList 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.
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.
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.
Author Miao, Zhiwei
Liang, Yushuang
Sun, Shengnan
Huang, Jing
Zhang, Ruilong
AuthorAffiliation State Key Laboratory, College of Chemistry
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
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Snippet Herein, we report a mild, one-pot method for silver-catalyzed tandem cycloisomerization/[5 + 2] cycloaddition reactions between readily accessible...
Herein, we report a mild, one-potmethod for silver-catalyzedtandemcycloisomerization/[5 + 2] cycloaddition reactions between readilyaccessible...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Silver-Catalyzed Tandem Cycloisomerization/[5 + 2] Cycloaddition of 3‑Cyclopropylideneprop-2-en-1-ones with Oxidopyrylium Ylides to Form Bibridged Benzocycloheptanones
URI http://dx.doi.org/10.1021/acs.joc.3c00436
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https://www.ncbi.nlm.nih.gov/pubmed/37364091
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