Title of article
Highly diastereoselective Claisen rearrangement leading to vicinal quaternary carbons construction of oxindoles
Author/Authors
Matsuta، نويسنده , , Yumiko and Kobari، نويسنده , , Takayuki and Kurashima، نويسنده , , Sachiko and Kumakura، نويسنده , , Yuhsuke and Shinada، نويسنده , , Masashi and Higuchi، نويسنده , , Kazuhiro and Kawasaki، نويسنده , , Tomomi، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
4
From page
6199
To page
6202
Abstract
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.
Keywords
Isomerization , cascade reactions , Spirooxindoles , Olefination
Journal title
Tetrahedron Letters
Serial Year
2011
Journal title
Tetrahedron Letters
Record number
1879568
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