Regio- and Diastereoselective Spirocyclopropanation of Benzofuran-Derived Azadienes through 1,4-Addition-Induced Dearomatization Reaction under Mild Conditions

A Cs2CO3-mediated [2 + 1] cycloaddition of benzofuran-derived azadienes (BDAs) with bromomalonate by using a dearomatization strategy has been developed. Through this process, BDAs serve as a potential 2-atom synthon in the construction of a range of functionalized spirocyclopropane derivatives, suc...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 13; pp. 5266 - 5270
Main Authors Fang, Qing-Yun, Yi, Meng-Hao, Wu, Xiao-Xia, Zhao, Li-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
ACID
ANNULATION
IMINES
CONSTRUCTION
CONJUGATE ADDITION
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Summary:A Cs2CO3-mediated [2 + 1] cycloaddition of benzofuran-derived azadienes (BDAs) with bromomalonate by using a dearomatization strategy has been developed. Through this process, BDAs serve as a potential 2-atom synthon in the construction of a range of functionalized spirocyclopropane derivatives, such as spirobenzofuran-2-cyclopropanes and spiroindane-2-cyclopropanes.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01987