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Asymmetric bis(oxazoline)–Ni(<scp>ii</scp>) catalyzed α-hydroxylation of cyclic β-keto esters under visible light

Hao Yin, Chaojie Wang, Yu-Gen Zhao, Zi‐Yang He, Mingming Chu, Yi-Feng Wang, Dan‐Qian Xu

2021Organic & Biomolecular Chemistry17 citationsDOI

Abstract

Using visible light as a driving force and molecular oxygen as a green oxidant, we developed bis(oxazoline)-Ni(acac)2 catalyzed asymmetric α-hydroxylation of β-keto esters under low photosensitizer loading, and the protocol enabled an efficient transformation to provide the desired chiral α-hydroxy-β-keto esters in high yields (up to 99%) and enantioselectivities (up to 99% ee) at room temperature.

Topics & Concepts

ChemistryHydroxylationOxazolineCatalysisStereochemistryCombinatorial chemistryOrganic chemistryEnzymeOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions
Asymmetric bis(oxazoline)–Ni(<scp>ii</scp>) catalyzed α-hydroxylation of cyclic β-keto esters under visible light | Litcius