Stereospecific ring expansion of chiral vinyl aziridines

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

Research output: Contribution to journalArticle

49 Citations (Scopus)

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

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Aziridines
Cyclization
expansion
Geometry
rings
products
geometry
aziridine
pyrroline

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Stereospecific ring expansion of chiral vinyl aziridines. / Brichacek, Matthew; Navarro Villalobos, Mauricio; Plichta, Alexandra; Njardarson, Jon T.

In: Organic Letters, Vol. 13, No. 5, 04.03.2011, p. 1110-1113.

Research output: Contribution to journalArticle

Brichacek, M, Navarro Villalobos, M, Plichta, A & Njardarson, JT 2011, 'Stereospecific ring expansion of chiral vinyl aziridines', Organic Letters, vol. 13, no. 5, pp. 1110-1113. https://doi.org/10.1021/ol200263g
Brichacek, Matthew ; Navarro Villalobos, Mauricio ; Plichta, Alexandra ; Njardarson, Jon T. / Stereospecific ring expansion of chiral vinyl aziridines. In: Organic Letters. 2011 ; Vol. 13, No. 5. pp. 1110-1113.
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