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 (-spiroepoxydienones) via the nucleophilic epoxidation of in situ generated -quinone methides from 4-(hydroxymethyl)phenols using aqueous HO. The developed protocol bypasses the need for stoichiometric bismuth reagents or diazomethane, which are frequently deployed for spiroepoxydienone preparation. The -spiroepoxydienones are further elaborated in numerous downstream complexity-building transformations.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6717626 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.9b02372 | DOI Listing |
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