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Gold-catalyzed preparation of annelated 2-azetidinones via divergent heterocyclization of enyne-tethered oxazolidines

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Abstract

The divergent and selective syntheses of two types of annelated β-lactams, namely, furan- and tetrahydropyridine-fused 2-azetidinones, have been accomplished directly from 2-azetidinone-tethered oxazolidine-enynes through gold catalysis. The decisive effect of the presence or absence of substituents at the enyne end has been disclosed. The gold-catalyzed conditions are mild enough to tolerate the selective formation of condensed β-lactams without the erosion of the stereochemical integrity of the products and without damaging the sensitive 2-azetidinone nucleus.

Graphical abstract: Gold-catalyzed preparation of annelated 2-azetidinones via divergent heterocyclization of enyne-tethered oxazolidines

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Publication details

The article was received on 19 Oct 2017, accepted on 28 Nov 2017 and first published on 29 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00950J
Citation: Org. Chem. Front., 2018, Advance Article
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    Gold-catalyzed preparation of annelated 2-azetidinones via divergent heterocyclization of enyne-tethered oxazolidines

    B. Alcaide, P. Almendros, T. Martínez del Campo and T. Naranjo, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00950J

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