title: Synthesis of Chiral Piperazinones Using Amphoteric Aziridine Aldehyde Dimers and Functionalized Isocyanides.
abstract: We have evaluated a range of functionalized isocyanides in the aziridine aldehyde-driven multicomponent synthesis of piperazinones. High diasteroselectivity for each isocyanide was observed. A theoretical evaluation of the reaction course corroborates the experimental data. Moreover, the reactivity of cis- and trans-configured aziridine aldehyde dimers has been compared. This study further probes the dimer-driven mechanism of cyclization and enables an efficient access to a wide range of chiral piperazinones bearing functionalized side chains.
authors.affiliation: Organic Chemistry Institute, Westfälische Wilhelms-Universität , Corrensstraße 40, 48149 Münster, Germany.
authors.forename: Niklas B
authors.initials: NB
authors.lastname: Heine
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6 Canada.
authors.forename: Sherif J
authors.initials: SJ
authors.lastname: Kaldas
authors.affiliation: Brock University , St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Lee
authors.initials: L
authors.lastname: Belding
authors.affiliation: Department of Chemistry, Lomonosov Moscow State University , 119899 Moscow, Russia.
authors.forename: Olga
authors.initials: O
authors.lastname: Shmatova
authors.affiliation: Brock University , St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Travis
authors.initials: T
authors.lastname: Dudding
authors.affiliation: Department of Chemistry, Lomonosov Moscow State University , 119899 Moscow, Russia.
authors.forename: Valentine G
authors.initials: VG
authors.lastname: Nenajdenko
authors.affiliation: Organic Chemistry Institute, Westfälische Wilhelms-Universität , Corrensstraße 40, 48149 Münster, Germany.
authors.forename: Armido
authors.initials: A
authors.lastname: Studer
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6 Canada.
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin