Stereospecific ring expansion of chiral vinyl aziridines

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

Research output: Contribution to journalArticle

50 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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