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Issue 43, 2018
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Morita–Baylis–Hillman reaction of a chiral aziridine aldehyde

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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.

Graphical abstract: Morita–Baylis–Hillman reaction of a chiral aziridine aldehyde

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Publication details

The article was received on 11 Jul 2018, accepted on 28 Aug 2018 and first published on 28 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01630E
Citation: Org. Biomol. Chem., 2018,16, 8048-8055
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    Morita–Baylis–Hillman reaction of a chiral aziridine aldehyde

    J. Lee, D. Singh and H. Ha, Org. Biomol. Chem., 2018, 16, 8048
    DOI: 10.1039/C8OB01630E

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