Iron-Catalyzed Asymmetric Inter- and Intramolecular Aerobic Oxidative Dearomatizing Spirocyclization of 2-Naphthols

Takuya Oguma, Daiki Doiuchi, Chisaki Fujitomo, Chungsik Kim, Hiroki Hayashi, Tatsuya Uchida, Tsutomu Katsuki

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)404-415
Number of pages12
JournalAsian Journal of Organic Chemistry
Volume9
Issue number3
DOIs
Publication statusPublished - Mar 1 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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