Stereospecific ring expansion of chiral vinyl aziridines

Matthew Brichacek, Mauricio Navarro Villalobos, Alexandra Plichta, Jon T. Njardarson

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis-or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.(Figure Presented)

Original languageEnglish (US)
Pages (from-to)1110-1113
Number of pages4
JournalOrganic Letters
Volume13
Issue number5
DOIs
StatePublished - Mar 4 2011

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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