Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones by coupling–isomerization–elimination (CIE) sequence

Christina Görgen née Boersch; Kiril Lutsenko; Eugen Merkul; Walter Frank; Thomas J. J. Müller

doi:10.1039/C6QO00138F

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Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones by coupling–isomerization–elimination (CIE) sequence†‡

Christina Görgen née Boersch,^a Kiril Lutsenko,^a Eugen Merkul,^a Walter Frank^b and Thomas J. J. Müller*^a

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^a Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
E-mail: ThomasJJ.Mueller@hhu.de

^b Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany

Abstract

N-Boc protected 1-aryl propargyl carbamates and acid chlorides can be readily transformed in a one-pot fashion by a coupling–isomerization–elimination (CIE) sequence into 4-substituted 5-(2-oxoethyl) oxazol-2(3H)-ones in moderate to good yield.

This article is part of the themed collection: Celebrating the 75th Birthday of Professor Barry Trost

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DOI: https://doi.org/10.1039/C6QO00138F
Article type: Research Article
Submitted: 01 Apr 2016
Accepted: 19 Mai 2016
First published: 19 Mai 2016
This article is Open Access

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Org. Chem. Front., 2016,3, 887-896

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Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones by coupling–isomerization–elimination (CIE) sequence

C. Görgen née Boersch, K. Lutsenko, E. Merkul, W. Frank and T. J. J. Müller, Org. Chem. Front., 2016, 3, 887 DOI: 10.1039/C6QO00138F

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Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones by coupling–isomerization–elimination (CIE) sequence†‡

Abstract

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Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones by coupling–isomerization–elimination (CIE) sequence

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