Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202300743
Keywords
Synthetic Methods; Rearrangement; Ring Expansion; Ketones; Bioisosteres
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A synthetic strategy involving Simmons-Smith cyclopropanation and 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.
A synthetic strategy involving a Simmons-Smith cyclopropanation, followed by an acid-catalyzed pinacol rearrangement, was developed to transform & alpha;-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.
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