Malonyl peroxides in organic synthesis (microreview)
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Malonyl peroxides in organic synthesis (microreview) Yana A. Barsegyan1, Vera A. Vil'1* 1
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia; е-mail: [email protected], [email protected] Submitted September 27, 2019 Accepted October 25, 2019
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(11), 1035–1037
A summary of the most recent applications of malonyl peroxides as reagents in organic synthesis is discussed. The microreview covers the latest selected examples on the usage of malonyl peroxides: dioxygenation and oxyamination of alkenes; oxidative C–O coupling with arenes, enol ethers, 1,3-dicarbonyl and N-heterocyclic compounds; sulfoxide synthesis.
Introduction Malonyl peroxides were first synthesized in 1971 by the group of professor Adam.1 Since that time, a significant amount of works were dedicated to the thermolysis, photolysis,2 and pyrolysis3 of malonyl peroxides. Cyclic structure and absence of an acidic proton favorably distinguish substituted malonyl peroxides from acyclic diacyl peroxides and peracids. Due to these features, one can expect an unusual properties of malonyl peroxides. In
Alkene dioxygenation A method for dihydroxylation of alkenes by the action of malonyl peroxides has been described by Tomkinson group.9 Syn-1,2-diols were prepared by the reaction of alkenes with cyclopropyl or cyclobutene malonyl peroxides in presence of H2O in CHCl3 or PhMe/RFOH medium followed by hydrolysis with 30–93% yield (up to syn:anti > 50:1).
the recent years, chemistry of malonyl peroxides has been studied intensively.4 This microreview contains data on the application of malonyl peroxides as reagents for stereoselective dioxygenation and oxyamination of alkenes with the formation of diols or heterocyclic compounds, as well as for sulfoxide synthesis. The oxidative C–O coupling of malonyl peroxides with arenes, various CH acids,5–8 and enol ethers are also discussed.
The reaction between homoallylic alcohols or carboxylic acids with cyclopropyl malonyl peroxide in HFIP led to the formation of tetrahydrofurans or γ-lactones with 44−82% yield and up to 27:1 trans selectivity.10
Yana A. Barsegyan was born in 1994 in Moscow, Russia. She graduated from Dmitry Mendeleev University of Chemical Technology of Russia in 2018. At present, she is PhD student under supervision of Prof. A. O. Terent'ev at the N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russia. Her research interests are chemistry of organic peroxides and oxidation processes. 0009-3122/19/55(11)-1035©2019 Springer Science+Business Media, LLC
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Vera A. Vil' was born in 1990 in Angarsk, Russia. She received her PhD in organic chemistry in 2017 under supervision of Prof. A. O. Terent'ev at the N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russia. At present, she is researcher at the same Institute. Her research interests are chemistry of organic peroxides, oxidation processes, and medicinal chemistry.
Chemistry of Heterocyclic Compounds 2019, 5
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