Novel ozone-mediated cleavage of the benzhydryl protecting group from aziridinyl esters.
[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.
Patwardhan
Aniruddha P
AP
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Lu
Zhenjie
Z
Pulgam
V Reddy
VR
Wulff
William D
WD
D001388:Aziridines / Q000737:chemistry*; D001559:Benzhydryl Compounds / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry*
D001388:Aziridines; D001559:Benzhydryl Compounds; D004952:Esters; D010126:Ozone