Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes
Correction(s) for this article
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Corrigendum: Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes
- Volume 57Issue 13Angewandte Chemie International Edition
- pages: 3281-3281
- First Published online: March 13, 2018
Jin Song
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
These authors contributed equally to this work.
Search for more papers by this authorZi-Jing Zhang
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Liu-Zhu Gong
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China
Search for more papers by this authorJin Song
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
These authors contributed equally to this work.
Search for more papers by this authorZi-Jing Zhang
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Liu-Zhu Gong
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 China
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China
Search for more papers by this authorGraphical Abstract
A team effort: An asymmetric [4+2] annulation of C1 ammonium enolates with copper–allenylidenes catalytically generated from carboxylic acids and 4-ethynyl dihydrobenzooxazinones, respectively, led to optically active 3,4-dihydroquinolin-2-one derivatives with excellent levels of stereoselectivity.
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.).
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