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Updated: Aug 11, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Novel ozone-mediated cleavage of the benzhydryl protecting group from aziridinyl esters
Aniruddha P Patwardhan1, Zhenjie Lu, V Reddy Pulgam
1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
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.
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