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.

Autor:	Hsu, Chih‐Wei, Lu, Yen‐Ting, Lin, Chi‐Ping, Yoo, Woo‐Jin
Předmět:	SILYL enol ethers PINACOL rearrangement CYCLOPROPANATION ENOL ethers BIOISOSTERES KETONES
Zdroj:	Advanced Synthesis & Catalysis; 9/19/2023, Vol. 365 Issue 18, p3082-3087, 6p
Abstrakt:	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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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