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

Jing Zhu | Zendy; Yi Yuan | Zendy; Shaozhong Wang | Zendy; ZhuJun Yao | Zendy

Open Access

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

Author(s) -

Jing Zhu,

Yi Yuan,

Shaozhong Wang,

ZhuJun Yao

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00749

Subject(s) - chemistry , thioether , alkene , alkyne , ether , tartaric acid , catalysis , photoredox catalysis , diastereomer , visible spectrum , cyclopropane , acetal , combinatorial chemistry , medicinal chemistry , organic chemistry , photochemistry , photocatalysis , materials science , ring (chemistry) , optoelectronics , citric acid

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 N -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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