Issue 44, 2022

Asymmetric dearomative cyclopropanation of naphthalenes to construct polycyclic compounds

Abstract

Catalytic asymmetric dearomatization (CADA) reactions is an important synthetic method for constructing enantioenriched complex cyclic systems from simple aromatic feedstocks. However, the CADA reactions of nonactivated arenes, such as naphthalenes and benzenes, have been far less explored than those of electronically activated arenes, such as phenols, naphthols and indoles. Herein, we disclose an asymmetric dearomative cyclopropanation of naphthalenes for the rapid construction of polycyclic compounds. With chiral dirhodium carboxylate as a catalyst, the dearomative cyclopropanation proceeded smoothly under mild conditions and afforded benzonorcaradiene-containing tetracycles in good yield and high enantioselectivity (up to 99% ee). Three stereogenic centers, including two all-carbon quaternary centers, were created in the dearomatization reaction. Moreover, a variety of functional groups are well-tolerated in the reaction. The products could be readily converted into other complex polycycles while maintaining the high ee value.

Graphical abstract: Asymmetric dearomative cyclopropanation of naphthalenes to construct polycyclic compounds

Supplementary files

Article information

Article type
Edge Article
Submitted
12 aug 2022
Accepted
11 okt 2022
First published
12 okt 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 13015-13019

Asymmetric dearomative cyclopropanation of naphthalenes to construct polycyclic compounds

F. Guan, R. Zhou, X. Ren, Z. Guo, C. Wang and C. Zhou, Chem. Sci., 2022, 13, 13015 DOI: 10.1039/D2SC04509E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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