title: Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes.
abstract: Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic systems from readily available precursors.
authors.affiliation: The Department of Chemistry, Chemistry Research Laboratory, The University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Nandkishor
authors.initials: N
authors.lastname: Chandan
authors.forename: Amber L
authors.initials: AL
authors.lastname: Thompson
authors.forename: Mark G
authors.initials: MG
authors.lastname: Moloney
mesh_terms: D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010091:Oximes; D011758:Pyrroles; D011759:Pyrrolidines; C013231:pyrroline