Highly diastereoselective Claisen rearrangement leading to vicinal quaternary carbons construction of oxindoles

An efficient approach to spirocyclic oxindole architecture with vicinal quaternary carbon centers is described. The reaction of 2-allyloxyindolin-3-ones with cyanomethylphosphonate at low reaction temperature proceeds smoothly with consecutive olefination, isomerization, deacylation, and anion-accel...

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Bibliographic Details
Published in:Tetrahedron letters 2011-11, Vol.52 (46), p.6199-6202
Main Authors: Matsuta, Yumiko, Kobari, Takayuki, Kurashima, Sachiko, Kumakura, Yuhsuke, Shinada, Masashi, Higuchi, Kazuhiro, Kawasaki, Tomomi
Format: Article
Language:English
Subjects:
Architecture
Carbon
Cascade reactions
Chemistry
Construction
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Isomerization
Olefination
Organic chemistry
Preparations and properties
Spirooxindoles
Tetrahedrons
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Summary:An efficient approach to spirocyclic oxindole architecture with vicinal quaternary carbon centers is described. The reaction of 2-allyloxyindolin-3-ones with cyanomethylphosphonate at low reaction temperature proceeds smoothly with consecutive olefination, isomerization, deacylation, and anion-accelerated Claisen rearrangement to give the 3,3-disubstituted oxindoles with vicinal quaternary all-carbon centers in high yield and diastereoselectivity. The oxindoles are readily converted into more synthetically advanced spiro-products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.09.059