Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides

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Abstract

Optically active aziridines were synthesized from the reaction of chiral nonracemic N-tert-butanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.

Original languageEnglish
Pages (from-to)65-80
Number of pages16
JournalUnknown Journal
Volume2010
Issue number7
DOIs
StatePublished - 2010

Keywords

  • Aziridines
  • N-sulfinyl imines
  • Phenyldiazomethane
  • Sulfur ylides

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