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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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Date
14/08/2016
Author
Barrios Antunez, Diego Javier
Greenhalgh, Mark David
Fallan, Charlene
Slawin, Alexandra Martha Zoya
Smith, Andrew David
Funder
European Commission
Grant ID
N/A
Keywords
QD Chemistry
DAS
Metadata
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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 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
DOI
https://doi.org/10.1039/C6OB01326K
ISSN
1477-0520
Type
Journal article
Rights
Copyright 2016 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1039/C6OB01326K
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
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/11129

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