Substituted cyclopropanols via sequential cyclopropanation and oxidative hydrolysis of vinylboronates

A scalable, diastereoselective protocol for synthesizing scarce 2-substituted cyclopropanols is presented. Our previous protocol for vinyl boron pinacolates cyclopropanation is adapted for flow conditions. This work establishes a fundamental understanding of both the stability of cyclopropanols under the formation conditions and the impact of the nature of the substituents on that stability.