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Synthesis of diketones, ketoesters and tetraketones by electrochemical oxidative decarboxylation of malonic acid derivatives: Application to the synthesis of cis-jasmone

Synthesis of diketones, ketoesters and tetraketones by electrochemical oxidative decarboxylation of malonic acid derivatives: Application to the synthesis of cis-jasmone

Ma, Xiaofeng, Dewez, Damien F., Du, Le, Luo, Xiya, Markó, István E. and Lam, Kevin ORCID: 0000-0003-1481-9212 (2018) Synthesis of diketones, ketoesters and tetraketones by electrochemical oxidative decarboxylation of malonic acid derivatives: Application to the synthesis of cis-jasmone. Journal of Organic Chemistry, 83 (19). pp. 12044-12055. ISSN 0022-3263 (Print), 1520-6904 (Online) (doi:https://doi.org/10.1021/acs.joc.8b01994)

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Abstract

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.

Item Type: Article
Uncontrolled Keywords: cis-jasmone, electrosynthesis, organic electrochemistry, synthesis, organic chemistry, diketones
Subjects: Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Last Modified: 31 Oct 2018 12:15
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/21549

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