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

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