Organo/Silver Dual Catalytic (3 + 2)/Conia-Ene Type Cyclization: Asymmetric Synthesis of Indane-Fused Spirocyclopenteneoxindoles

Developing efficient strategies to synthesize spirocyclopenteneoxindoles is an attractive target due to their potential biological activity. This work described the thiourea/silver dual catalytic (3 + 2)/Conia-ene type reaction of 2-(2-oxoindolin-3-yl)­malononitrile with ortho-ethynyl substituted ni...

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Published inOrganic letters Vol. 24; no. 33; pp. 6197 - 6201
Main Authors Li, Dong-Ai, He, Xiang-Hong, Tang, Xue, Wu, Yuling, Zhao, Hongli, He, Gu, Peng, Cheng, Han, Bo, Zhan, Gu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.08.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CARBENE
COOPERATIVE CATALYSIS
BETA-KETOESTERS
ALKYNES
CONIA-ENE
CONSTRUCTION
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Summary:Developing efficient strategies to synthesize spirocyclopenteneoxindoles is an attractive target due to their potential biological activity. This work described the thiourea/silver dual catalytic (3 + 2)/Conia-ene type reaction of 2-(2-oxoindolin-3-yl)­malononitrile with ortho-ethynyl substituted nitrostyrene. The reaction features mild conditions and good atom- and step-economy. Three new C–C bonds were formed within one synthetic step, providing the indane-fused spirocyclopenteneoxindoles in good yields, with excellent chemo-, regio-, and stereoselectivity.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02472