PMID: 11312948Apr 21, 2001Paper

Reverse aromatic cope rearrangement of 2-allyl-3-alkylideneindolines driven by olefination of 2-allylindolin-3-ones: synthesis of alpha-allyl-3-indole acetate derivatives

The Journal of Organic Chemistry
T KawasakiM Sakamoto

Abstract

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 alpha-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.

References

Nov 15, 1996·The Journal of Organic Chemistry·Vincent J. Santora, Harold W. Moore

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Citations

Sep 30, 2003·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Masanori SakamotoOsamu Tamura
Apr 27, 2016·Journal of the American Chemical Society·Xuerong YuTuoping Luo
Mar 3, 2021·Organic & Biomolecular Chemistry·Breanna M Tomiczek, Alexander J Grenning

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