title: Stereocontrolled disruption of the Ugi reaction toward the production of chiral piperazinones: substrate scope and process development.
abstract: The factors determining diastereoselectivity observed in the multicomponent conversion of amino acids, aziridine aldehyde dimers, and isocyanides into chiral piperazinones have been investigated. Amino acid-dependent selectivity for either trans- or cis-substituted piperazinone products has been achieved. An experimentally determined diastereoselectivity model for the three-component reaction driven by aziridine aldehyde dimers has predictive value for different substrate classes. Moreover, this model is useful in reconciling the previously reported observations in multicomponent reactions between isocyanides, α-amino acids, and monofunctional aldehydes.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
authors.forename: Serge
authors.initials: S
authors.lastname: Zaretsky
authors.forename: Shinya
authors.initials: S
authors.lastname: Adachi
authors.forename: Benjamin H
authors.initials: BH
authors.lastname: Rotstein
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Hickey
authors.forename: Conor C G
authors.initials: CC
authors.lastname: Scully
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: St Denis
authors.forename: Rebecca
authors.initials: R
authors.lastname: Courtemanche
authors.forename: Joy C Y
authors.initials: JC
authors.lastname: Yu
authors.forename: Benjamin K W
authors.initials: BK
authors.lastname: Chung
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D054659:Diketopiperazines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D001388:Aziridines; D003486:Cyanides; D054659:Diketopiperazines; C033132:aziridine