Construction of an isoquinolinone framework from carboxylic-ester-directed umpolung ring opening of methylenecyclopropanes

An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to real...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 57; no. 85; pp. 1121 - 1124
Main Authors Wei, Hao-Zhao, Wei, Yin, Shi, Min
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 26.10.2021
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Ring opening
Science & Technology
ACTIVATION
SULFUR
ALKYLIDENECYCLOPROPANES
CYCLIZATION
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Summary:An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to realize an umpolung ring opening of the MCP. This work established an operationally convenient protocol for the rapid construction of isoquinolinone frameworks. A novel carboxylic ester directed umpolung ring opening of functionalized methylenecyclopropanes (MCPs) leading to the rapid construction of isoquinolinone framework.
Bibliography:2091583
For ESI and crystallographic data in CIF or other electronic format see DOI
2074397
Electronic supplementary information (ESI) available: Detailed experimental procedures and analytical data. CCDC
and
10.1039/d1cc04826k
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc04826k