3 years ago

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

Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes
Liu-Zhu Gong, Zi-Jing Zhang, Jin Song
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.). 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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700105

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