Highly chemo- and enantioselective inter- and intra-molecular oxidative dearomatizing spirocyclization of 1-alkyl-2-naphthols with O2 as the hydrogen acceptor was achieved using an iron catalyst. In the iron complex 1-catalyzed reaction, 1-methyl-2-naphthols 2 in the presence of phenol derivatives as the nucleophile was selectively oxidized, producing the spirocyclic ketones with good to high enantioselectivities via a tandem strategy. Pre-synthesized 1,1′-methylbis(arenol)s 6 and 7, intermediates of the tandem strategy were also converted to the desired products with chemo- and enantioselectivity.
All Science Journal Classification (ASJC) codes
- Organic Chemistry