Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

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 appl...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 19; pp. 12044 - 12055
Main Authors Ma, Xiaofeng, Dewez, Damien F, Du, Le, Luo, Xiya, Markó, István E, Lam, Kevin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.10.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY NITROALKANES
KETONES
REAGENTS
ACYL ANION
FURANS
1,4-DICARBONYL COMPOUNDS
CHEMISTRY
STETTER REACTION
CYCLOPENTENONES
CONJUGATE ADDITION
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01994