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

Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9886-9890. doi: 10.1002/anie.201705530. Epub 2017 Jul 12.

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.

Keywords: aziridination; dirhodium catalysis; hydroxylamine-O-sulfonic acid; nitrenoids; olefins.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Aziridines / chemical synthesis*
  • Aziridines / chemistry
  • Catalysis
  • Hydroxylamines / chemistry*
  • Molecular Structure
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Aziridines
  • Hydroxylamines
  • hydroxylamine-O-sulfonic acid
  • Rhodium