Phenolic Oxidation Using H2 O2 via in Situ Generated para -Quinone Methides for the Preparation of para -Spiroepoxydienones

Organic Letters
Michael F McLaughlinJeffrey S Johnson

Abstract

Phenols are attractive starting materials for the preparation of highly substituted cyclohexane rings via dearomative processes. Herein we report an efficient preparation of dearomatized 1-oxaspiro[2.5]octa-4,7-dien-6-ones (para-spiroepoxydienones) via the nucleophilic epoxidation of in situ generated para-quinone methides from 4-(hydroxymethyl)phenols using aqueous H2O2. The developed protocol bypasses the need for stoichiometric bismuth reagents or diazomethane, which are frequently deployed for p-spiroepoxydienone preparation. The p-spiroepoxydienones are further elaborated in numerous downstream complexity-building transformations.

References

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Sep 7, 2006·Journal of the American Chemical Society·Emily E WeinertSteven E Rokita
Apr 21, 2011·Angewandte Chemie·Stéphane P Roche, John A Porco
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Aug 4, 2018·Chemical Society Reviews·William C WertjesDavid Sarlah
Jan 31, 2019·Journal of the American Chemical Society·Michael F McLaughlinJeffrey S Johnson

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Citations

Feb 13, 2020·Chemical Communications : Chem Comm·Kyu TerashimaTakashi Yamazaki
Feb 14, 2020·Organic & Biomolecular Chemistry·Blessing D Deeyaa, Steven E Rokita
Mar 24, 2020·Nature Chemistry·Muhammet UyanikKazuaki Ishihara

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