title: Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks.
abstract: This paper describes the first study of solution-phase synthesis of chiral monosubstituted piperazine building blocks from nosylamide-activated aziridines. The protocol, involving aminolysis of the starting aziridines with omega-amino alcohols and subsequent Fukuyama-Mitsunobu cyclization, offers the advantage of mild conditions as well as short reaction times, and it leads to optically pure N-Boc- or N-Ns-protected piperazines. This four-step sequence, requiring only a single final chromatographic purification, was extended to include novel diazepane and diazocane derivatives.
authors.affiliation: Department of Medicinal Chemistry, University of Copenhagen, Universitetsparken 2, Copenhagen DK-2100, Denmark.
authors.forename: François
authors.initials: F
authors.lastname: Crestey
authors.forename: Matthias
authors.initials: M
authors.lastname: Witt
authors.forename: Jerzy W
authors.initials: JW
authors.lastname: Jaroszewski
authors.forename: Henrik
authors.initials: H
authors.lastname: Franzyk
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry; D015394:Molecular Structure; D000077489:Piperazine; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C545228:1,4-diazepane; D001381:Azepines; D001388:Aziridines; D010879:Piperazines; D000077489:Piperazine