title: Novel ozone-mediated cleavage of the benzhydryl protecting group from aziridinyl esters.
abstract: [reaction: see text]. N-Benzhydryl aziridines-2-carboxylates can be readily obtained from the catalytic asymmetric aziridination reaction from N-benzhydrylimines and ethyl diazoacetate. Cleavage of the benzhydryl group by hydrogenolysis leads to ring opening when R = aryl. Surprisingly, ozone will selectively oxidize the benhydryl group in these aziridines even when R is an aryl group. This allows for a new deprotection strategy for these aziridines whose generality is explored.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
authors.forename: Aniruddha P
authors.initials: AP
authors.lastname: Patwardhan
authors.forename: Zhenjie
authors.initials: Z
authors.lastname: Lu
authors.forename: V Reddy
authors.initials: VR
authors.lastname: Pulgam
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D001559:Benzhydryl Compounds / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry*
chemical_list: D001388:Aziridines; D001559:Benzhydryl Compounds; D004952:Esters; D010126:Ozone