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Updated: Feb 5, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Morita-Baylis-Hillman reaction of a chiral aziridine aldehyde
Jaedeok Lee1, Deepak Singh, Hyun-Joon Ha
1Department of Chemistry, Hankuk University of Foreign Studies, Yongin, 17035 Korea. hjha@hufs.ac.kr.
Abstract:
The Morita-Baylis-Hillman reaction of (R)-1-((R)-1-phenylethyl)aziridine-2-carbaldehyde with alkyl acrylate was carried out under various conditions by changing solvents, bases, and alcohol additives. The reaction at room temperature under neat conditions (no solvent) with quinuclidine as an amine nucleophile, in the presence of benzyl alcohol as an additive, afforded a product, γ-(aziridin-2-yl)-β-hydroxy-α-methylene butanoate, in 97% yield with a diastereomeric ratio of anti and syn as 86 : 14.
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