Synthesis
DOI: 10.1055/a-2402-6757
feature

Aza-BODIPY-Based Bifunctional Photocatalyst for Red-Light-Driven Asymmetric Hydroxylation of β‑Ketoesters

Yonghong Guo
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei University, Baoding 071002, P. R. of China
,
Jiayi Zhao
b   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
,
Bing Zu
b   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
,
Chuan He
b   Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. of China
› Author Affiliations
The National Natural Science Foundation of China (22122102, 22271134), Guangdong Provincial Key Laboratory of Catalysis (2020B121201002), Guangdong Pearl River Talent Program (2019QN01Y628), Shenzhen Science and Technology Innovation Commission (RCJC20221008092723013, JCYJ20230807093104009), and Hebei Province Innovation Capability Enhancement Plan Project (22567632H).


Abstract

A novel bifunctional photocatalyst combining an aza-BODIPY and a chiral oxazoline has been developed. This photocatalyst enables the asymmetric hydroxylation of β‑ketoesters under an oxygen atmosphere and irradiation with 18-W red LEDs. This procedure offers a convenient and potentially general approach to obtain enantioenriched α-hydroxy-β-dicarbonyl products. The results reported in this manuscript demonstrate the promise of this new organic photocatalyst design and will help expand the application of BODIPY-based chiral photocatalysts.

Supporting Information



Publication History

Received: 31 May 2024

Accepted after revision: 23 August 2024

Accepted Manuscript online:
23 August 2024

Article published online:
26 September 2024

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