Issue 51, 2017

A highly enantioselective access to chiral chromanones and thiochromanones via copper-catalyzed asymmetric conjugated reduction of chromones and thiochromones

Abstract

The chromanone scaffold is a privileged structure in heterocyclic chemistry and drug discovery. A highly efficient copper-catalyzed asymmetric conjugated reduction of chromones is developed to give chiral chromanones with good yields (80–99%) and excellent ee values (94–>99% ee). Particularly noteworthy is that chiral thiochromanones are also constructed using this method in 74–87% yields with 96–97% ee. The established asymmetric synthesis paves the way for their further pharmaceutical studies.

Graphical abstract: A highly enantioselective access to chiral chromanones and thiochromanones via copper-catalyzed asymmetric conjugated reduction of chromones and thiochromones

Supplementary files

Article information

Article type
Communication
Submitted
22 May 2017
Accepted
31 May 2017
First published
31 May 2017

Chem. Commun., 2017,53, 6844-6847

A highly enantioselective access to chiral chromanones and thiochromanones via copper-catalyzed asymmetric conjugated reduction of chromones and thiochromones

D. Xiong, W. Zhou, Z. Lu, S. Zeng and J. (. Wang, Chem. Commun., 2017, 53, 6844 DOI: 10.1039/C7CC03939E

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