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Phase‐Transfer‐Catalyzed Oxaziridine‐Mediated Hydroxylative Phenol and Naphthol Dearomatization
Author(s) -
Grandclaudon Charlotte,
Toullec Patrick Y.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501340
Subject(s) - chemistry , chemoselectivity , phenols , catalysis , phenol , hydroxylation , organic chemistry , alkyl , base (topology) , alcohol , medicinal chemistry , combinatorial chemistry , mathematical analysis , mathematics , enzyme
A new methodology for the dearomative ortho ‐hydroxylation of substituted phenolic substrates is reported. In the presence of a phase‐transfer catalyst and a base, N ‐sulfonyloxaziridines react with phenols to give the corresponding 6‐alkyl‐6‐hydroxycyclohexadienone products in moderate to good yields. The reaction proceeds in fair to good yields and excellent chemoselectivity for 2,6‐disubstituted phenols, 1‐naphthols, and 2‐naphthols.