Issue 24, 2023
From the journal:

Chemical Communications

Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts†

Qing-Xia Zhang,a   Jia-Hao Xie,a   Qing Gua  and  Shu-Li You ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, China
E-mail: slyou@sioc.ac.cn

Abstract

An asymmetric allylic dearomatization reaction of 1-nitro-2-naphthol derivatives with Morita–Baylis–Hillman (MBH) adducts has been developed. By utilizing Pd catalyst derived from Pd(OAc)2 and Trost ligand (R,R)-L1, the reaction proceeded smoothly in 1,4-dioxane at room temperature, affording substituted β-naphthalenones in good yields (up to 92%) and enantioselectivity (up to 90% ee). A range of substituted 1-nitro-2-naphthols and MBH adducts were found to be compatible under the optimized conditions. This reaction provides a convenient method for the synthesis of enantioenriched 1-nitro-β-naphthalenone derivatives.

Graphical abstract: Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts

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Article information

DOI
https://doi.org/10.1039/D3CC00568B
Article type
Communication
Submitted
07 Feb 2023
Accepted
01 Mar 2023
First published
01 Mar 2023
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2023,59, 3590-3593

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Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts

Q. Zhang, J. Xie, Q. Gu and S. You, Chem. Commun., 2023, 59, 3590 DOI: 10.1039/D3CC00568B

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