Issue 15, 2019

Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst

Abstract

The Ir-catalyzed highly efficient asymmetric hydrogenation of benzoxazinones and derivatives was successfully developed with N-methylated ZhaoPhos L5 as the ligand, which may display a new activation mode with a single anion-binding interaction among the substrate, cocatalyst Brønsted acid and ligand. This synthetic approach afforded a series of chiral dihydrobenzoxazinones and derivatives with excellent results (>99% conversion, 88–96% yields, 91–>99% ee, up to 40 500 TON). A key to success is the utilization of a strong Brønsted acid as the cocatalyst, such as hydrochloric acid, to form a possible single anion-binding interaction with the substrate and catalyst, which greatly contributed to the improvement of reactivity and enantioselectivity. Importantly, a creative and efficient synthetic route was developed to construct the important intermediate for the potential IgE/IgG receptor modulator through our catalytic methodology system.

Graphical abstract: Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst

Supplementary files

Article information

Article type
Edge Article
Submitted
28 Dec 2018
Accepted
03 Mar 2019
First published
19 Mar 2019
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., 2019,10, 4328-4333

Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst

Z. Han, G. Liu, R. Wang, X. Dong and X. Zhang, Chem. Sci., 2019, 10, 4328 DOI: 10.1039/C8SC05797D

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements