Stereoselective Dehydroxyboration of Allylic Alcohols to Access (E)-Allylboronates by a Combination of C-OH Cleavage and Boron Transfer under Iron Catalysis

Iron-catalyzed direct S(N)2' dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation. The six-membered ring transition state formed by allylic alcohols and iron-boron intermediate was indicated to be the key component involved in transfer of the boron group, activation of the C-OH bond, and control of the stereoselectivity.

Automated summary

Iron-catalyzed direct S(N)2' dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. The key component involved in this transformation is the six-membered ring transition state formed by allylic alcohols and iron-boron intermediate, which controls the transfer of the boron group and the stereoselectivity.