113446-72-3Relevant academic research and scientific papers
A Dual Regiocontrol in the Copper-catalysed Grignard Reaction with Primary Allylic Acetates
Baeckvall, Jan-E.,Sellen, Michael
, p. 827 - 829 (1987)
The reaction of primary allylic acetates with Grignard reagents in the presence of catalytic amounts of Li2CuCl4 can be regiochemically controlled to give either α- or γ-substitution of the allylic acetoxy group.
Regiocontrol in copper-catalyzed grignard reactions with allylic substrates
B?ckvall, Jan-E.,Sellén, Mikael,Grant, Brian
, p. 6615 - 6621 (2007/10/02)
The regiochemistry of copper-catalyzed reactions between Grignard reagents and allylic substrates has been studied. A dual regiocontrol was obtained in the Li2CuCl4-catalyzed Grignard reaction with primary allylic acetates. Reaction
The use of metal reagents in stereo- and regioselective functionalizations of conjugated dienes
Baeckval, Jan-E
, p. 665 - 670 (2007/10/02)
Conjugated dienes have been selectively functionalized via 1-acetoxy-4-chloro-2-alkenes and via 2-(phenylsulfonyl)-1,3-dienes.In both these approaches nucleophiles can be added to the 1- and 4-positions.It was shown that also non-stabilized carbon nucleophiles (from cuprates or copper(I)-catalyzed Grignard reactions) can be used.The utility of the functionalizations was demonstrated by the syntheses of a marine natural product and a butterfly pheromone.Finally, the 2-(phenyl-sulfonyl)-1,3-dienes show a dual electron demand in Diels-Alder reactions and give cycloadducts with both electron-rich and electron-deficient olefins.
