126156-63-6Relevant academic research and scientific papers
Alkylation of Allylic Derivatives. 14. Relationship of Double-Bond Configuration between Reactant and Product for Cross-Coupling Reactions of Z-Allylic Carboxylates with Organocopper Reagents
Underiner, Ted L.,Paisley, Steven D.,Schmitter, Joel,Lesheski, Larry,Goering, Harlan L.
, p. 2369 - 2374 (2007/10/02)
Cross-coupling reactions of alkylcuprates (sp3 reagents) with allylic carboxylates can result in loss of double-bond configuration in the α-alkylation product.Loss of configuration occurs during the reaction, which shows that an intermediate is involved in which the double bond is temporarily relocated.With phenyl- and vinylcuprates (sp2 reagents) the original double-bond configuration is fully preserved in all cases.This shows that the original double bond is partly retained throughout the reaction.Evidently with sp2 reagents, oxidative addition leads directly to a ?-allylcopper(III) complex (12).
