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Reaction of N-heterocyclic carbaldehydes with furanones – An investigation of reactivity and regioselectivity

Author:
Uhrner, Fabian, Lederle, Felix, Namyslo, Jan C., Gjikaj, Mimoza, Schmidt, Andreas, Hübner, Eike G.
Source:
Tetrahedron 2017
ISSN:
0040-4020
Subject:
aldehydes, chemical reactions, chemical structure, lactones, nuclear magnetic resonance spectroscopy
Abstract:
The aldol reaction of N-heterocyclic carbaldehydes with furan-2-ones has been investigated. Very mild and metal-free reaction conditions have been applied. The substitution pattern of the product was found to be controlled by the aldehyde. A detailed investigation of the reactivity has been performed and the surprising regio- and diastereoselectivity has been elucidated with the help of 2D-NMR techniques. Here, we report on a convenient way to N-donor functionalized lactones, which had scarcely been examined before.
Agid:
5705581