Rhodium-Catalyzed Sequential Cycloisomerization/Aldol Addition of Cyclopropene Carboxylic Acids with Isatins

A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected is...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 14; pp. 5600 - 5604
Main Authors Zhang, Dan, Wang, Xin, Zhang, Mengchu, Hu, Wenhao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.07.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CARBENOIDS
BUTENOLIDES
FURANS
H BOND INSERTION
3-COMPONENT REACTION
RING
CHEMISTRY
YLIDES
DERIVATIVES
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Summary:A unique, rhodium-catalyzed reaction of cyclopropene carboxylic acids with isatins has been developed, which takes place through a trapping process of transient cyclic carboxylic oxonium ylides. This reaction tolerates a wide variety of cyclopropene carboxylic acids and N-protected or unprotected isatins and represents a new, direct strategy to access valuable γ-substituted γ-butenolide architectures containing an oxindole moiety in very high yields under mild reaction conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01957