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Updated: Jun 8, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Ring opening of pymisyl-protected aziridines with organocuprates
Jan Bornholdt1, Jakob Felding, Rasmus P Clausen
1Department of Medicinal Chemistry, University of Copenhagen, Faculty of Pharmaceutical Sciences, Universitetsparken 2, 2100 Copenhagen, Denmark.
Abstract:
The pyrimidine-2-sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl-protected 2-methyl-aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment with a thiolate. The versatility of this new nitrogen protecting group is illustrated with a new synthesis of Selegiline, a monoamine oxidase-B inhibitor marketed for the treatment of Parkinson's disease.
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