Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans.
[reaction: see text] Mild Ni(0)-catalyzed rearrangements of 1-acyl-2-vinylcyclopropanes have been developed. The room-temperature isomerizations afford dihydrofuran products in yields regularly greater than 90%. A highly substituted, stereochemically defined cyclopropane was employed in the rearrangement to evaluate the reaction mechanism. Product analysis indicates that the overall reaction proceeds with retention of configuration at the vinyl-bearing stereogenic center.
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Roy K
RK
Bowman
Jeffrey S
JS
Johnson