Issue 42, 2018

Catalytic enantioselective radical coupling of activated ketones with N-aryl glycines

Abstract

Asymmetric H-bonding catalysis as a viable strategy for enantioselective radical coupling of ketones is demonstrated. With a visible-light-mediated dual catalytic system involving a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and a chiral phosphoric acid (CPA), N-aryl glycines with a variety of 1,2-diketones and isatins underwent a redox-neutral radical coupling process and furnished two series of valuable chiral 1,2-amino tertiary alcohols in high yields with good to excellent enantioselectivities (up to 97% ee). In this catalysis platform, the formation of neutral radical intermediates between ketyl and H-bonding catalyst CPA is responsible for presenting stereocontrolling factors. Its success in this work should provide inspiration for expansion to other readily accessible ketones to react with various radical species, thus leading to a productive approach to access chiral tertiary alcohol derivatives.

Graphical abstract: Catalytic enantioselective radical coupling of activated ketones with N-aryl glycines

Supplementary files

Article information

Article type
Edge Article
Submitted
04 7 2018
Accepted
27 8 2018
First published
27 8 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 8094-8098

Catalytic enantioselective radical coupling of activated ketones with N-aryl glycines

Y. Liu, X. Liu, J. Li, X. Zhao, B. Qiao and Z. Jiang, Chem. Sci., 2018, 9, 8094 DOI: 10.1039/C8SC02948B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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