Synthesis of Bicyclo[2.1.1]hexan‐5‐ones via a Sequential Simmons‐Smith Cyclopropanation and an Acid‐Catalyzed Pinacol Rearrangement of α‐Hydroxy Silyl Enol Ethers

Abstract

AbstractA synthetic strategy involving a Simmons‐Smith cyclopropanation, followed by an acid‐catalyzed pinacol rearrangement, was developed to transform α‐hydroxy silyl enol ethers into 1‐substituted bicyclo[2.1.1]hexan‐5‐ones. These bicyclic ketones underwent further synthetic manipulations to generate various 1,5‐disubstituted bicyclo[2.1.1]hexanes, which could serve as potential bioisosteres of ortho‐substituted arenes.