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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Dearomatization/Spiroannulation of Halophenols Enables the Forging of Contiguous Quaternary Carbon Cyclohexadienones
Sichan Dong1, Changzhen Fu1, Yicong Ge1,2
1Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China.
Abstract:
A dearomatization/spiroannulation process has been successfully achieved between simple halophenols and α,β-unsaturated olefins under mild reaction conditions. This transformation addresses the chemoselectivity issue in the dearomatizative transformation of phenol scaffolds (6π-electron) caused by the SEAr process, enabling the construction of versatile cyclohexadienone frameworks containing contiguous quaternary all-carbon centers in high yields. Further studies have provided valuable insights into the process, revealing that debromination/spiroannulation occurs through the SRN1 pathway.
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