Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst.

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ID: 26444
2019
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Abstract
Copper-based asymmetric photocatalysis has great potential in the development of green synthetic approaches to chiral molecules. However, there are several formidable challenges associated with such a conception. These include the relatively weak visible light absorption, short excited-state lifetimes, incompatibility of different catalytic cycles, and the difficulty of the stereocontrol. We report here an effective strategy by means of single-electron-transfer (SET) initiated formation of radicals and photoactive intermediates to address the long-standing problems. Through elaborate selection of well-matched reaction partners, the chiral bisoxazoline copper catalyst is engaged in the SET process, photoredox catalysis, Lewis acid activation and asymmetric induction. Accordingly, a highly enantioselective photocatalytic α-aminoalkylation of acyclic imine derivatives has been accessed. This strategy sheds light on how to make use of diverse functions of a single transition metal catalyst in one reaction, and offers an economic and simplified approach to construction of highly valuable chiral vicinal diamines.
Reference Key
han2019photocatalyticnature Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Han, Bowen;Li, Yanjun;Yu, Ying;Gong, Lei;
Journal Nature communications
Year 2019
DOI
10.1038/s41467-019-11688-7
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