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Issue 30, 2016
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Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

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Abstract

The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96 : 4 dr, 95 : 5 er) via intramolecular Michael addition has been developed using keto–enone substrates and a bifunctional tertiary amine–thiourea catalyst. This methodology was extended to include non-activated ketone pro-nucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.

Graphical abstract: Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

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Publication details

The article was received on 20 Jun 2016, accepted on 30 Jun 2016 and first published on 08 Jul 2016


Article type: Paper
DOI: 10.1039/C6OB01326K
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 7268-7274
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    Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

    D. Barrios Antúnez, M. D. Greenhalgh, C. Fallan, A. M. Z. Slawin and A. D. Smith, Org. Biomol. Chem., 2016, 14, 7268
    DOI: 10.1039/C6OB01326K

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