Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed Ring-Opening Formal [3 + 2]-Cycloaddition of Spirovinylcyclopropyl Oxindole and 3‑Oxindole Derivatives

A palladium-catalyzed ring-opening oxo-formal [3 + 2]-cycloaddition reaction of novel donor–acceptor spirovinylcyclopropyl oxindole with 3-oxindole is described. The developed protocol provides facile access to oxo-bispirooxindole derivatives in good yields (up to 82% yield) with excellent diastereo...

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Published inJournal of organic chemistry Vol. 84; no. 4; pp. 2297 - 2306
Main Authors Xiao, Jun-An, Li, Yu-Chun, Luo, Zhi-Jin, Cheng, Xiu-Liang, Deng, Zhi-Xiong, Chen, Wen-Qiang, Su, Wei, Yang, Hua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.02.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIELS-ALDER REACTIONS
DIASTEREOSELECTIVE SYNTHESIS
ISATINS
STEREOCENTERS
DONOR-ACCEPTOR CYCLOPROPANE
1,3-DIPOLAR CYCLOADDITION
VINYL CYCLOPROPANES
ENANTIOSELECTIVE CONSTRUCTION
3+2 CYCLOADDITION
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Summary:A palladium-catalyzed ring-opening oxo-formal [3 + 2]-cycloaddition reaction of novel donor–acceptor spirovinylcyclopropyl oxindole with 3-oxindole is described. The developed protocol provides facile access to oxo-bispirooxindole derivatives in good yields (up to 82% yield) with excellent diastereoselectivities (up to 20:1 dr).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02889