Synthesis of Dissymmetric Malonic Acid Monoamides from Symmetric Dithiomalonates

Hisashi Wauke, Kazumasa Matsuo, Kenji Matsumoto, Mitsuru Shindo

Research output: Contribution to journalArticle

Abstract

We report a highly selective synthesis of dissymmetric S,N-malonates from symmetric dithiomalonates under mild conditions. This reaction was accelerated using a Cu(II) catalyst developed by us. When an aliphatic amine was used as the nucleophile, the amine also worked as a base and accelerated the amination reaction. Kinetic studies indicated that the key step of this reaction is the thermal formation of an acylketene; its stability mainly contributes to the selectivity of the reaction. The synthetic utility of dissymmetric S,N-malonates is also shown by the synthesis of linomide.

Original languageEnglish
Pages (from-to)6830-6833
Number of pages4
JournalChemistrySelect
Volume1
Issue number21
DOIs
Publication statusPublished - Jan 1 2016

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Malonates
Amines
Amination
Nucleophiles
Catalysts
Kinetics
malonic acid

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Synthesis of Dissymmetric Malonic Acid Monoamides from Symmetric Dithiomalonates. / Wauke, Hisashi; Matsuo, Kazumasa; Matsumoto, Kenji; Shindo, Mitsuru.

In: ChemistrySelect, Vol. 1, No. 21, 01.01.2016, p. 6830-6833.

Research output: Contribution to journalArticle

Wauke, Hisashi ; Matsuo, Kazumasa ; Matsumoto, Kenji ; Shindo, Mitsuru. / Synthesis of Dissymmetric Malonic Acid Monoamides from Symmetric Dithiomalonates. In: ChemistrySelect. 2016 ; Vol. 1, No. 21. pp. 6830-6833.
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