Stereoselective amination: Via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine

Yuta Sadamitsu, Kodai Saito, Tohru Yamada

Research output: Contribution to journalArticle

Abstract

The stereoselective synthesis of aminovinyloxazolidinones based on the electrophilic amination of a vinyl-silver intermediate, generated by silver-catalyzed carbon dioxide incorporation on a propargyl amine, was achieved. The geometry of the aminated product was determined by a single crystal X-ray analysis and NOE measurement and it was elucidated that the geometry was proved to be opposite to the geometry predicted from the previous silver-catalyzed carbon dioxide fixation on a propargyl amine derivative. This unexpected stereoselectivity could be successfully explained by a radical mechanism. This journal is

Original languageEnglish
Pages (from-to)9517-9520
Number of pages4
JournalChemical Communications
Volume56
Issue number66
DOIs
Publication statusPublished - 2020 Aug 25

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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