Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones

Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones

A simple route to complexity: An organocatalytic 1,3‐dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate....

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Veröffentlicht in:Angewandte Chemie International Edition 2013-08, Vol.52 (33), p.8633-8637
Hauptverfasser: Sun, Wangsheng, Zhu, Gongming, Wu, Chongyang, Li, Guofeng, Hong, Liang, Wang, Rui
Format: Artikel
Sprache:eng
Schlagworte:
1,3‐dipolar cycloaddition
3-dipolar cycloaddition
asymmetric synthesis
Aza Compounds - chemistry
azlactones
Catalysis
Complexity
Cyclization
Cycloaddition
Cycloaddition Reaction
Ethers
Indoles - chemistry
Lactones - chemistry
Magnetic Resonance Spectroscopy
methyleneindolinones
Molecular Structure
Nuclei
organocatalysis
Spiro Compounds - chemistry
Stereoisomerism
Transformations
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Zusammenfassung:A simple route to complexity: An organocatalytic 1,3‐dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. Bn=benzyl, HOBt=1‐hydroxy‐1H‐benzotriazole, MTBE=methyl tert‐butyl ether, PG=protecting group, TMS=trimethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201302831