Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes.

ABSTRACT: Dimethylcyclopropanes are valuable synthetic targets that are challenging to access in high yield using Zn carbenoid reagents. Herein, we describe a cobalt-catalyzed variant of the Simmons-Smith reaction that enables the efficient dimethylcyclopropanation of 1,3-dienes using a Me₂ CCl₂ /Zn reagent mixture. The reactions proceed with high regioselectivity based on the substitution pattern of the 1,3-diene. The products are vinylcyclopropanes, which serve as substrates for transition-metal-catalyzed ring-opening reactions, including 1,3-rearrangement and [5+2] cycloaddition. Preliminary studies indicate that moderately activated monoalkenes are also amenable to dimethylcyclopropanation under the conditions of cobalt catalysis.

SUBMITTER: Werth J 

PROVIDER: S-EPMC6489504 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature