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Updated: Jun 20, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Tandem asymmetric Aza-Darzens/ring-opening reactions: dual functionality from the silane lewis acid
S Corey Valdez1, James L Leighton
1Department of Chemistry, Columbia University, New York, New York 10027, USA.
Abstract:
The addition of a stabilized sulfur ylide (generated by the rhodium-catalyzed reaction of Ph(2)S with ethyl diazoacetate) to N-acylhydrazones promoted by a chiral silane Lewis acid leads to the highly diastereo- and enantioselective synthesis of beta-chloro-alpha-hydrazido esters. The addition of electron-rich arenes and ZnCl(2) to the reaction mixture leads to the highly diastereo- and enantioselective one-pot synthesis of diarylalanine derivatives. In both cases, the silane Lewis acid responsible for the first reaction performs the second function of activating the aziridine intermediate toward nucleophilic attack.
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