Synthesis of 2,3-Dialkylated Tartaric Acid Esters via Visible Light Photoredox-Catalyzed Reductive Dimerization of α-Ketoesters.

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ID: 26436
2017
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Abstract
A mild transition-metal-free protocol to prepare 2,3-dialkylated tartaric acid esters has been developed by taking advantage of a visible light photoredox-catalyzed reductive dimerization of α-ketoesters with a combination of an organic dye photocatalyst and a Hantzsch-type 1,4-dihydropyridine hydrogen donor. A broad range of functional groups including cyclopropane, alkene, alkyne, 4-methoxybenzyl ether, acetal, silyl ether, carbamate, cyclic ether, cyclic thioether, bromoalkane, and -alkoxyphthalimide are well-compatible. By employing the visible light photoredox-catalyzed reductive coupling and the subsequent optical resolution, both enantioenriched diastereomers of 2,3-dialkylated tartaric acid could be acquired conveniently.
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zhu2017synthesisacs Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Zhu, Jing;Yuan, Yi;Wang, Shaozhong;Yao, Zhu-Jun;
Journal ACS omega
Year 2017
DOI
10.1021/acsomega.7b00749
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