From isonitrile to nitrile via ketenimine intermediate: Palladium-catalyzed 1,1-carbocyanation of allyl carbonate by α-isocyanoacetate
A palladium-catalyzed 1,1-carbocyanation of allyl carbonate by α-quaternary α-isocyanoacetate was developed. Formation of ketenimine followed by homolysis of the C–N bond and recombination of the resulting caged radical pair was proposed to account for the formation of the unusual coupling product, the β-cyano-γ,δ-unsaturated ester.
Synthesis of new cyclopropylisonitriles and their applications in Ugi four-component reactions
Several new cyclopropylisonitriles were synthesized from the corresponding cyclopropylamines (41-69% yield) and utilized in Ugi four-component reactions to furnish 12 new dipeptides in 38-86% yield. The structures of four of these dipeptides were determined by X-ray crystallography. Georg Thieme Verlag Stuttgart.
Osipova, Anna,Yufit, Dmitrii S.,De Meijere, Armin
p. 131 - 139
(2008/01/03)
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