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Updated: Jan 21, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Two Distinct Ag(I)- and Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines
Rahul Dadabhau Kardile1, Rai-Shung Liu1
1Frontier Research Center on Fundamental and Applied Sciences of Matters, Department of Chemistry , National Tsing-Hua University , Hsinchu , Taiwan, ROC.
Abstract:
Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.
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