title: Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine.
abstract: Starting from chiral-protected 4-hydroxymethyl pyrrolidin-2-ones, the otherwise elusive 3,4-trans-3,3,4-trisubstituted isosteres of α-methyl homoserine, tethered on a γ-lactam ring, were prepared exploiting stereoselective electrophilic aminations. These reactions led to the isolation and characterization of a novel type of atropisomers, exceedingly stable at room temperature, that were directly converted to the desired products by a novel non-reductive N-N bond cleavage reaction.
authors.affiliation: Department of Life and Environmental Sciences, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Amabili
authors.affiliation: Department of Odontostomatologic and Specialized Clinical Sciences, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy.
authors.forename: Adolfo
authors.initials: A
authors.lastname: Amici
authors.affiliation: Department of Life and Environmental Sciences, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy.
authors.forename: Annafelicia
authors.initials: A
authors.lastname: Civitavecchia
authors.affiliation: Department of Life and Environmental Sciences, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy.
authors.forename: Beatrice
authors.initials: B
authors.lastname: Maggiore
authors.affiliation: Department of Life and Environmental Sciences, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy.
authors.forename: Mario
authors.initials: M
authors.lastname: Orena
authors.affiliation: Department of Life and Environmental Sciences, Università Politecnica delle Marche, Via Brecce Bianche, 60131, Ancona, Italy. s.rinaldi@univpm.it.
authors.forename: Samuele
authors.initials: S
authors.lastname: Rinaldi
authors.affiliation: Department of Chemistry ''G. Ciamician'', Alma Mater Studiorum University of Bologna, Via Selmi 2, 40126, Bologna, Italy.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Tolomelli
mesh_terms: D000586:Amination; D006714:Homoserine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D006714:Homoserine
keywords: Amination; Atropisomers; Isosteres; Stereoselectivity; γ-Lactams