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Issue 15, 2017
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Selective synthesis of mono- and bis-butenolide α-aminomethyl adducts

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Abstract

The selective installation of α-methylamine residues at the butenolide core is described using α-bromomethylene-γ-butenolide and primary as well as secondary amines in methanol at 0 °C. The preparation of mono- and bis-butenolide α-adducts is described. Bis-γ-butenolide adducts as well as mono α-aminomethyl-γ-butenolides can be selectively obtained depending on the nature of the reacting primary amine. In contrast, the use of secondary amines allows two different pathways leading either to the expected amino derivatives or to the formation of a C–O bond.

Graphical abstract: Selective synthesis of mono- and bis-butenolide α-aminomethyl adducts

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Publication details

The article was received on 25 Jan 2017, accepted on 22 Mar 2017 and first published on 22 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00206H
Org. Biomol. Chem., 2017,15, 3298-3303

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    Selective synthesis of mono- and bis-butenolide α-aminomethyl adducts

    A. Talbi, A. Arfaoui, T. Bsaibess, M. Lotfi Efrit, A. Gaucher, D. Prim and H. M′Rabet, Org. Biomol. Chem., 2017, 15, 3298
    DOI: 10.1039/C7OB00206H

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