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Updated: Mar 15, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Passerini Reactions on Biocatalytically Derived Chiral Azetidines
Lisa Moni1, Luca Banfi2, Andrea Basso3
1Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy. lisa.moni@unige.it.
Abstract:
The purpose of this study was to explore a series of Passerini reactions on a biocatalytically derived enantiopure azetidine-2-carboxyaldehyde in order to obtain, in a diastereoselective manner, polyfunctionalised derivatives having the potential to be cyclized to chiral bridged bicyclic nitrogen heterocycles. While diastereoselectivity was poor under classical Passerini conditions, a significant increase of diastereoselectivity (up to 76:24) was gained by the use of zinc bromide as promoter. The methodology has a broad scope and yields are always good.
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