title: Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: a one-carbon homologative relay ring expansion.
abstract: An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Schomaker
authors.forename: Somnath
authors.initials: S
authors.lastname: Bhattacharjee
authors.forename: Jun
authors.initials: J
authors.lastname: Yan
authors.forename: Babak
authors.initials: B
authors.lastname: Borhan
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003622:Dapsone / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D011759:Pyrrolidines; C036115:sulfoxone; D003622:Dapsone