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

Diego Javier Barrios Antunez, Mark David Greenhalgh, Charlene Fallan, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)7268-7274
Number of pages7
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number30
Early online date8 Jul 2016
DOIs
Publication statusPublished - 14 Aug 2016

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