Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 May 2;56(19):5212-5216.
doi: 10.1002/anie.201700105. Epub 2017 Mar 31.

Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes

Jin Song  1 , Zi-Jing Zhang  1 , Liu-Zhu Gong  1   2
Affiliations

Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes

Jin Song et al. Angew Chem Int Ed Engl. .

Erratum in

Abstract

An asymmetric catalytic decarboxylative [4+2] annulation of 4-ethynyl dihydrobenzooxazinones and carboxylic acids has been established by cooperative copper and nucleophilic Lewis base catalysis. A C1 ammonium enolate and copper-allenylidene complex, each catalytically generated from different substrates, underwent a cascade asymmetric propargylation and lactamization process to yield optically active 3,4-dihydroquinolin-2-one derivatives with excellent levels of stereoselectivity (up to 99 % ee, 95:5 d.r.).

Keywords: C1 ammonium enolates; [4+2] annulations; cooperative catalysis; copper; heterocycles.

PubMed Disclaimer

Publication types

LinkOut - more resources