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Updated: Feb 22, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine
Tanya Napolitano1, Shu-Yuan Cheng1,2, Brooke Nielsen1
1John Jay College of Criminal Justice, New York, 524 west 59 Street, New York, NY, 10019, USA.
Abstract:
A 2-protected cis-amino mitosene undergoes an irreversible acetone promoted isomerization and converts to the 1-isomer. Kinetic studies and DFT calculations of the reaction are reported. An organocatalytic mechanism is proposed, involving a covalent intermediate formed by reaction of the mitosene and acetone.
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