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. 2006 Feb 16;8(4):573-6.
doi: 10.1021/ol052700k.

Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans

Roy K Bowman  1 , Jeffrey S Johnson
Affiliations

Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans

Roy K Bowman et al. Org Lett. .

Abstract

[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.

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