Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst
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 pronucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.
Citation
Barrios Antunez , D J , Greenhalgh , M D , Fallan , C , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst ' , Organic & Biomolecular Chemistry , vol. 14 , no. 30 , pp. 7268-7274 . https://doi.org/10.1039/C6OB01326K
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
ISSN
1477-0520Type
Journal article
Description
The research leading to these results (D-J.B.A.; C. F.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013) / ERC grant agreement n° 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award.Collections
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