title: Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent.
abstract: The regioselective lithiation-functionalization of 2-arylazetidines has been explored. The nature of the N-substituent is mainly responsible for a regioselectivity switch. ortho-Lithiation occurred, using hexyllithium as a greener base, in N-alkylazetidines, while α-benzylic lithiation has been observed with N-Boc azetidines.
authors.affiliation: Department of Pharmacy - Drug Sciences, University of Bari, "A. Moro" Via E. Orabona 4, Bari 70125, Italy. renzo.luisi@uniba.it leonardo.degennaro@uniba.it.
authors.forename: Leonardo
authors.initials: L
authors.lastname: Degennaro
authors.forename: Marina
authors.initials: M
authors.lastname: Zenzola
authors.forename: Piera
authors.initials: P
authors.lastname: Trinchera
authors.forename: Laura
authors.initials: L
authors.lastname: Carroccia
authors.forename: Arianna
authors.initials: A
authors.lastname: Giovine
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Romanazzi
authors.forename: Aurelia
authors.initials: A
authors.lastname: Falcicchio
authors.forename: Renzo
authors.initials: R
authors.lastname: Luisi
mesh_terms: D001384:Azetidines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001384:Azetidines; D009584:Nitrogen