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Issue 37, 2017
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Cerium-catalyzed, oxidative synthesis of annulated, tetrasubstituted dihydrofuran-derivatives

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Abstract

Densely functionalized, annulated dihydrofuran derivatives are prepared by a cerium-catalyzed aerobic oxidation reaction. The operationally simple transformation is environmentally and economically benign, since the precatalyst CeCl3·7H2O is non-toxic and inexpensive and the oxidant is simply dioxygen from air. Starting materials are β-oxoesters and silylenolethers, and the latter are derived from acetoacetate or acetylacetone. The reaction sequence is performed in one flask and consists of α-oxidation and Mukaiyama aldol reaction. Apart from tetrahydrocyclopenta[b]furan derivatives one example of a tetrahydrofuro[3,4-b]furan and one tetrahydro-3aH-furo[2,3-c]pyrrole derivative are prepared.

Graphical abstract: Cerium-catalyzed, oxidative synthesis of annulated, tetrasubstituted dihydrofuran-derivatives

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Publication details

The article was received on 31 Jul 2017, accepted on 22 Aug 2017 and first published on 23 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01904A
Citation: Org. Biomol. Chem., 2017,15, 7824-7829
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    Cerium-catalyzed, oxidative synthesis of annulated, tetrasubstituted dihydrofuran-derivatives

    I. Geibel, M. Schmidtmann and J. Christoffers, Org. Biomol. Chem., 2017, 15, 7824
    DOI: 10.1039/C7OB01904A

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