title: Lithiation of N-alkyl-(o-tolyl)aziridine: stereoselective synthesis of isochromans.
abstract: The lithiation reaction of o-tolylaziridine 1 has been investigated by using the aziridine ring capability to act as a directing metalation group. Trapped with electrophiles, the resulting o-aziridinyl benzyllithium 1-Li gives access to several functionalized aziridines 2a-j. The hydroxyalkylated derivatives 2d-j were converted into important scaffolds such as isochromans 3a-d. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been developed starting from enantioenriched o-tolylaziridine.
authors.affiliation: Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi C.I.N.M.P.I.S., Via E. Orabona 4, I-70125-Bari, Italy.
authors.forename: Mariangela
authors.initials: M
authors.lastname: Dammacco
authors.forename: Leonardo
authors.initials: L
authors.lastname: Degennaro
authors.forename: Saverio
authors.initials: S
authors.lastname: Florio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
authors.forename: Biagia
authors.initials: B
authors.lastname: Musio
authors.forename: Angela
authors.initials: A
authors.lastname: Altomare
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000737:chemistry*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D002839:Chromans; C033132:aziridine; D008094:Lithium