Claisen Rearrangement through Enolization of 2-Allyloxyindolin-3-ones: Construction of Adjacent Carbon Stereocenters in 3-Hydroxyindolin-2-ones

Abstract The Claisen rearrangement of 3-oxy-2-allyloxyindoles through base-induced enolization of 2-allyloxyindolin-3-ones was investigated. This rearrangement reaction proceeded smoothly at low temperature and showed intriguing diastereoselectivity that did not depend on the initial olefin geometry...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2010-11, Vol.2010 (21), p.3609-3614
Main Authors: Higuchi, Kazuhiro, Saito, Keita, Hirayama, Tetsuya, Watanabe, Yoshiaki, Kobayashi, Emiko, Kawasaki, Tomomi
Format: Article
Language:English
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Summary:Abstract The Claisen rearrangement of 3-oxy-2-allyloxyindoles through base-induced enolization of 2-allyloxyindolin-3-ones was investigated. This rearrangement reaction proceeded smoothly at low temperature and showed intriguing diastereoselectivity that did not depend on the initial olefin geometry.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1258208