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

Meiqi Geng; Jinqiang Kuang; Maozhong Miao; Yongmin Ma

doi:10.1039/d3ob00296a

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

Org Biomol Chem. 2023 Apr 12;21(15):3101-3104. doi: 10.1039/d3ob00296a.

Authors

Meiqi Geng^{1

2}, Jinqiang Kuang¹, Maozhong Miao², Yongmin Ma¹

Affiliations

¹ Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang 318000, Zhejiang, China. jinqiangkuang@163.com.
² 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. mmzok@hotmail.com.

PMID: 37000579
DOI: 10.1039/d3ob00296a

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.