Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems

Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio-and diastereoselective hydro or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivered the title compounds.

Automated summary

Here, we demonstrate a method to form acyclic frameworks with two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This approach involves regio-and diastereoselective hydro or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes by adding nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivers the desired compounds.