Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids

Zhiwei Ma, Zhe Zhou, László Kürti

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

A RhII-catalyzed direct and stereospecific N-H- and N-alkyl aziridination of olefins is reported that uses hydroxylamine-O-sulfonic acids as inexpensive, readily available, and nitro group-free aminating reagents. Unactivated olefins, featuring a wide range of functional groups, are converted into the corresponding N-H or N-alkyl aziridines in good to excellent yields. This operationally simple, scalable transformation proceeds efficiently at ambient temperature and is tolerant towards oxygen and trace moisture.

Original languageEnglish (US)
Pages (from-to)9886-9890
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number33
DOIs
StatePublished - Jan 1 2017

Keywords

  • aziridination
  • dirhodium catalysis
  • hydroxylamine-O-sulfonic acid
  • nitrenoids
  • olefins

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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