TY - JOUR
T1 - Iron-Catalyzed Asymmetric Inter- and Intramolecular Aerobic Oxidative Dearomatizing Spirocyclization of 2-Naphthols
AU - Oguma, Takuya
AU - Doiuchi, Daiki
AU - Fujitomo, Chisaki
AU - Kim, Chungsik
AU - Hayashi, Hiroki
AU - Uchida, Tatsuya
AU - Katsuki, Tsutomu
N1 - Funding Information:
Financial Support from JSPS KAKENHI Grant Number JP16H01033 and 18H04264 in Precisely Designed Catalysis with Customized Scaffolding; The International Institute for Carbon-Neutral Energy Research (WP-I2CNER) from MEXT, Japan, are grateful acknowledged. T. O. is grateful for the JSPS Research Fellowships for Young Scientists.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/3/1
Y1 - 2020/3/1
N2 - 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.
AB - 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.
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U2 - 10.1002/ajoc.201900602
DO - 10.1002/ajoc.201900602
M3 - Article
AN - SCOPUS:85076540867
SN - 2193-5807
VL - 9
SP - 404
EP - 415
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 3
ER -