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Updated: Jun 12, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Facile approach to optically active alpha-alkylidene-beta-amino esters by thermal Overman rearrangement
Sung Il Lee1, Soon Young Moon, Geum-Sook Hwang
1Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea.
Abstract:
A convenient synthetic method for enantioenriched (E)-alpha-alkylidene-beta-amino esters has been developed through thermal Overman rearrangement. Readily accessible (Z)-beta-branched Morita-Baylis-Hillman esters serve as chiral pool precursors. Thermal rearrangement proceeded through a concerted pseudopericyclic transition state to produce (E)-stereoselective products. We expanded the synthetic utilities of alpha-alkylidene-beta-amino esters via preparation of alpha-alkylidene-beta-lactam derivatives.
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