title: Synthesis of optically active arylaziridines by regio- and stereospecific lithiation of N-bus-phenylaziridine.
abstract: Alpha,alpha-disubstituted aziridines can be produced in good yields by selective lithiation of N-tert-butylsulfonyl-2-phenylaziridine (n-BuLi/TMEDA, Et(2)O) at the benzylic position and subsequent trapping with a range of electrophiles. Repetition of the lithiation/electrophilic trapping sequence provides a stereocontrolled route to trisubstituted aziridines. Using (R)-N-tert-butylsulfonyl-2-phenylaziridine, the alpha,alpha-disubstituted aziridines can be produced as single enantiomers (er >98:2), indicating that the intermediate organolithium is configurationally stable. Efficient aziridine ring-opening reactions leading to 1,2-diamines and 1,4-diamines are also reported.
authors.affiliation: Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, UK.
authors.forename: Biagia
authors.initials: B
authors.lastname: Musio
authors.forename: Guy J
authors.initials: GJ
authors.lastname: Clarkson
authors.forename: Michael
authors.initials: M
authors.lastname: Shipman
authors.forename: Saverio
authors.initials: S
authors.lastname: Florio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009904:Optical Rotation; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001388:Aziridines; C033132:aziridine; D008094:Lithium