Issue 37, 2017

Cerium-catalyzed, oxidative synthesis of annulated, tetrasubstituted dihydrofuran-derivatives

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Jul 2017
Accepted
22 Aug 2017
First published
23 Aug 2017

Org. Biomol. Chem., 2017,15, 7824-7829

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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