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Cobalt-Catalyzed Asymmetric Hydrosilylation of α-Oxygenated Ketones

Huiting Wen, Yifei Chen, Lanxuan Shi, Jianhui Chen*, Yanshu Luo and Yuanzhi Xia*

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China, Email: cjhwzu.edu.cn, xyzwzu.edu.cn

H. Wen, Y. Chen, L. Shi, J. Chen, Y. Luo, Y. Xia, Org. Lett., 2023, 25, 2184-2189.

DOI: 10.1021/acs.orglett.3c00162


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Abstract

The combination of Co(OAc)2 with a chiral phosphine-amido-oxazoline (PAO) ligand catalyzes a mild and efficient asymmetric hydrosilylation of α-oxygenated ketones to provide synthetically useful 1,2-diol derivatives. The optically enriched products can be converted into chiral α-hydroxy acids, 1,3-dioxolan-2-ones, ethylene oxides, and 1,2,3-1H-triazoles.

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proposed mechanism



Key Words

reduction of carbonyl compounds, diphenylsilane, benzoates


ID: J54-Y2023