Reverse Aromatic Cope Rearrangement of 2-Allyl-3-alkylideneindolines Driven by Olefination of 2-Allylindolin-3-ones:  Synthesis of α-Allyl-3-indole Acetate Derivatives

The reverse aromatic Cope rearrangement of 2-allyl-3-alkylideneindolines obtained by Horner−Wadsworth−Emmons olefination of 2-allylindolin-3-ones was performed. When 2-allylindolin-3-ones were treated with phosphonium ylides in refluxing toluene, domino Wittig reaction and reverse aromatic Cope rear...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-02, Vol.66 (4), p.1200-1204
Main Authors: Kawasaki, Tomomi, Nonaka, Yoshinori, Watanabe, Kazuaki, Ogawa, Atsuyo, Higuchi, Kazuhiro, Terashima, Romi, Masuda, Kouhei, Sakamoto, Masanori
Format: Article
Language:English
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Summary:The reverse aromatic Cope rearrangement of 2-allyl-3-alkylideneindolines obtained by Horner−Wadsworth−Emmons olefination of 2-allylindolin-3-ones was performed. When 2-allylindolin-3-ones were treated with phosphonium ylides in refluxing toluene, domino Wittig reaction and reverse aromatic Cope rearrangement took place to give α-allyl-3-indole acetate derivatives in good yields. The aromatization as a new driving force in the Cope rearrangement is preferable to the conjugation with the carbonyl and cyano groups and also to the alkyl substitution pattern, which are well-known driving forces.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0014921