Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids

Kohei Sekine, Takanori Mawatari, Tohru Yamada

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Highly Z-selective syntheses of oxazolidin-2-ones from propargylic alcohols containing internal alkynes and phenyl isocyanate were achieved by using a combination of silver acetate and N,N-dimethylaminopyridine. The catalytic system was applied to propargylic alcohols containing alkyl-substituted alkyne groups. By considering the results in the presence and absence of an electron-withdrawing group on the aromatics, it was shown that the silver catalyst effectively activates the C≡C triple bond by acting as a π-Lewis acid to produce the corresponding oxazolidinones with high Z-selectivities.

Original languageEnglish
Article numberst-2015-u0506-l
Pages (from-to)2447-2450
Number of pages4
JournalSynlett
Volume26
Issue number17
DOIs
Publication statusPublished - 2015 Oct 22

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Oxazolidinones
Lewis Acids
Alkynes
Cyclization
Silver
Alcohols
Catalysts
Electrons
phenyl isocyanate
silver acetate

Keywords

  • catalysis
  • cyclizations
  • isocyanates
  • oxazolidinones
  • silver
  • tandem reactions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids. / Sekine, Kohei; Mawatari, Takanori; Yamada, Tohru.

In: Synlett, Vol. 26, No. 17, st-2015-u0506-l, 22.10.2015, p. 2447-2450.

Research output: Contribution to journalArticle

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