1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols

The development ofnew methods and protocols for thesynthesisof biologically active substances remains one of the most importantpillars in organic chemistry, and one of these privileged structuralmotifs are allylic alcohols. The method of choice to date for thesynthesis of these is the Nozaki-Hiyama-Takai-Kishireaction. We describe here a valuable alternative to the synthesisof allylic alcohols via 1,2-metallate rearrangement. In this work,various vinyl boronic esters with different functional groups havebeen applied in the Hoppe-Matteson-Aggarwal reaction.In addition, two monoterpenoids were constructed via this convergentsynthetic strategy.

Automated summary

The development of new methods and protocols for the synthesis of biologically active substances, such as allylic alcohols, remains crucial in organic chemistry. The Nozaki-Hiyama-Takai-Kishi reaction is currently the preferred method for their synthesis. This study presents an alternative approach through 1,2-metallate rearrangement and demonstrates the successful synthesis of allylic alcohols using various vinyl boronic esters. Additionally, two monoterpenoids were synthesized using this convergent synthetic strategy.