Organocatalytic asymmetric multicomponent cascade reaction via 1,3-proton shift and [3+2] cycloaddition: an efficient strategy for the synthesis of oxindole derivatives

An efficient and powerful organocatalytic cascade reaction was achieved for the synthesis of biologically important chiral spiro[pyrrolidin-3,2'-oxindoles] using very simple and readily available starting materials. Three C-C bonds and four contiguous stereogenic centers including one quaternar...

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Published inChemical communications (Cambridge, England) Vol. 49; no. 65; pp. 7213 - 7215
Main Authors Tian, Li, Hu, Xiu-Qin, Li, Yun-Han, Xu, Peng-Fei
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2013
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cycloaddition Reaction
Indoles - chemistry
Physical Sciences
Protons
Science & Technology
Spiro Compounds - chemistry
Stereoisomerism
ISATIN
BIOMIMETIC TRANSAMINATION
HYDROGENATION
AMINO-ACIDS
ALPHA-KETO ESTERS
FACILE
HIGHLY EFFICIENT
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Summary:An efficient and powerful organocatalytic cascade reaction was achieved for the synthesis of biologically important chiral spiro[pyrrolidin-3,2'-oxindoles] using very simple and readily available starting materials. Three C-C bonds and four contiguous stereogenic centers including one quaternary stereocenter were established in a single operation with reasonable yields and good stereoselectivity.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc43755h