Issue 15, 2023
From the journal:

Organic & Biomolecular Chemistry

Cu(ii)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon†

Meiqi Geng,ab   Jinqiang Kuang, ORCID logo *a   Maozhong Miao ORCID logo b  and  Yongmin Ma ORCID logo *a  

* Corresponding authors

a Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang 318000, Zhejiang, China
E-mail: jinqiangkuang@163.com, yongmin.ma@tzc.edu.cn

b Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, P. R. China
E-mail: mmzok@hotmail.com

Abstract

Herein, a Cu(II)-catalyzed facile construction of synthetically valuable spiro compounds from β-naphthols in air is reported, in which N,N-dimethylaminoethanol (DMEA) serves as an efficient and unique C1 synthon. This transformation proceeds through an ortho-quinone methide (o-QM) formation/Michael addition/dearomatization sequence, affording various spiro(naphthalenenaphtho)furan-2-ones in moderate to excellent yields.

Graphical abstract: Cu(ii)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon

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Article information

DOI
https://doi.org/10.1039/D3OB00296A
Article type
Communication
Submitted
23 Feb 2023
Accepted
14 Mar 2023
First published
27 Mar 2023

Org. Biomol. Chem., 2023,21, 3101-3104

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Cu(II)-catalyzed domino construction of spironaphthalenones by dearomatization of β-naphthols and using N,N-dimethylaminoethanol as a C1 synthon

M. Geng, J. Kuang, M. Miao and Y. Ma, Org. Biomol. Chem., 2023, 21, 3101 DOI: 10.1039/D3OB00296A

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