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
Journal
Advanced Synthesis and Catalysis
Journal Volume
365
Journal Issue
18
Pages
3082
Date Issued
2023-09-19
Author(s)
Abstract
A 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.
Subjects
Bioisosteres | Ketones | Rearrangement | Ring Expansion | Synthetic Methods
Type
journal article