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Updated: Jun 20, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Enantioselective chemoenzymatic synthesis of trans-aziridines
Bas Ritzen1, Matthijs C M van Oers, Floris L van Delft
1Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, NL-6525 AJ Nijmegen, The Netherlands.
Abstract:
A straightforward, five-step procedure for the synthesis of enantiomerically pure 2,3-disubstituted trans-aziridines has been developed starting from commercially available aldehydes. Hydroxynitrile lyase-mediated cyanohydrin formation provided cyanohydrins in excellent enantioselectivities and good yields. Subsequent formation of diastereomerically pure anti-amino alcohols via a one-pot Grignard addition-reduction sequence, Cu(II)-catalyzed diazotransfer, and triphenylphosphine-mediated reductive cyclization provided the corresponding trans-aziridines in good yields and excellent diastereoselectivities.
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