Highly selective aziridination of imines using trimethylsilyldiazomethane and applications of C-silylaziridines in synthesis

VK Aggarwal*, Marco Ferrara

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

71 Citations (Scopus)

Abstract

[GRAPHICS]

Trimethylsilyldiazomethane has been found to add directly to N-sulfonyl (Ts and SES) imines to afford aziridines in good yields and high cis stereoselectivities. The silyl group can be substituted by treatment with a fluoride source and electrophiles again with high selectivity. Complete regioselectivity is observed in ring opening of these aziridines with nucleophiles.

Translated title of the contributionHighly Selective Aziridination of Imines Using Trimethylsilyldiazomethane and Applications of C-Silylaziridines in Synthesis
Original languageEnglish
Pages (from-to)4107-4110
Number of pages4
JournalOrganic Letters
Volume2
Issue number25
DOIs
Publication statusPublished - 14 Dec 2000

Keywords

  • ASYMMETRIC AZIRIDINATION
  • ETHYL DIAZOACETATE
  • LEWIS-ACID
  • METHYLRHENIUM TRIOXIDE
  • OLEFINS
  • COMPLEXES
  • ESTERS
  • CATALYSTS
  • AZIRINE
  • ALKENES

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