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

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 var...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-09, Vol.365 (18), p.3082-3087
Main Authors: Hsu, Chih‐Wei, Lu, Yen‐Ting, Lin, Chi‐Ping, Yoo, Woo‐Jin
Format: Article
Language:English
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300743