title: Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.
abstract: s-BuLi-induced α-lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Christopher I
authors.initials: CI
authors.lastname: Pearson
authors.forename: Madiha
authors.initials: M
authors.lastname: Kazmi
mesh_terms: D001385:Azetines / Q000138:chemical synthesis* / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001385:Azetines; C000590472:N-Boc-2-lithio-2-azetine; D009942:Organometallic Compounds; D003300:Copper; D008094:Lithium