Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones

Kohei Sekine, Ryo Kobayashi, Tohru Yamada

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for the stereoselective synthesis of (E)-iodovinyloxazolidinones was developed. The silver-catalytic system could be applied to various propargylic amines to afford the corresponding iodovinyloxazolidinones in high yields. The structure of the oxazolidinone was confirmed by X-ray structure analysis to be the Eisomer for the geometry of the exo-olefin. The silver-catalyzed cyclization and replacement of silver with the iodine group in the intermediate were thought to be crucial steps.

Original languageEnglish
Pages (from-to)1407-1409
Number of pages3
JournalChemistry Letters
Volume44
Issue number10
DOIs
Publication statusPublished - Jan 1 2015
Externally publishedYes

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Silver
Carbon Dioxide
Amines
Oxazolidinones
Cyclization
Alkenes
Iodine
X rays
Geometry
N-iodosuccinimide

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones. / Sekine, Kohei; Kobayashi, Ryo; Yamada, Tohru.

In: Chemistry Letters, Vol. 44, No. 10, 01.01.2015, p. 1407-1409.

Research output: Contribution to journalArticle

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