Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N′-dioxide–scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology co...

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Autores principales: Zhang, Yu, Liao, Yuting, Liu, Xiaohua, Xu, Xi, Lin, Lili, Feng, Xiaoming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5625263/
https://www.ncbi.nlm.nih.gov/pubmed/28989691
http://dx.doi.org/10.1039/c7sc02809a
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author Zhang, Yu
Liao, Yuting
Liu, Xiaohua
Xu, Xi
Lin, Lili
Feng, Xiaoming
author_facet Zhang, Yu
Liao, Yuting
Liu, Xiaohua
Xu, Xi
Lin, Lili
Feng, Xiaoming
author_sort Zhang, Yu
collection PubMed
description An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N′-dioxide–scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.
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spelling pubmed-56252632017-10-06 Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives Zhang, Yu Liao, Yuting Liu, Xiaohua Xu, Xi Lin, Lili Feng, Xiaoming Chem Sci Chemistry An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N′-dioxide–scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed. Royal Society of Chemistry 2017-09-01 2017-07-24 /pmc/articles/PMC5625263/ /pubmed/28989691 http://dx.doi.org/10.1039/c7sc02809a Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Zhang, Yu
Liao, Yuting
Liu, Xiaohua
Xu, Xi
Lin, Lili
Feng, Xiaoming
Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
title Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
title_full Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
title_fullStr Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
title_full_unstemmed Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
title_short Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
title_sort catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5625263/
https://www.ncbi.nlm.nih.gov/pubmed/28989691
http://dx.doi.org/10.1039/c7sc02809a
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