American Chemical Society
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Stereospecific Ring Expansion of Chiral Vinyl Aziridines

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posted on 2011-03-04, 00:00 authored by Matthew Brichacek, Mauricio Navarro Villalobos, Alexandra Plichta, Jon T. Njardarson
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.