biostudies-literatureBrichacek MNIGMS NIH HHS1110-3https://www.ebi.ac.uk/biostudies/studies/S-EPMC3072884biostudies-literatureUnknown13(5)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.Organic lettersStereospecific ring expansion of chiral vinyl aziridines.PMC3072884T32GM008500T32 GM008500-11T32 GM008500Brichacek MNjardarson JTVillalobos MNPlichta AfalseStereospecific ring expansion of chiral vinyl aziridines.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.2011-01-01T00:00:00Z2011 Mar2020-11-01T08:15:35Z2019-03-27T00:40:29ZS-EPMC30728842130952810.1021/ol200263g