title: Stereospecific ring expansion of chiral vinyl aziridines.
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.
authors.affiliation: Department of Chemistry and Chemical Biology, Cornell University , Ithaca, New York 14853, USA.
authors.forename: Matthew
authors.initials: M
authors.lastname: Brichacek
authors.forename: Mauricio Navarro
authors.initials: MN
authors.lastname: Villalobos
authors.forename: Alexandra
authors.initials: A
authors.lastname: Plichta
authors.forename: Jon T
authors.initials: JT
authors.lastname: Njardarson
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D001388:Aziridines; D011758:Pyrroles; D014753:Vinyl Compounds; C013231:pyrroline