title: 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 pro-nucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors.forename: Diego-Javier
authors.initials: DJ
authors.lastname: Barrios Antúnez
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors.forename: Mark D
authors.initials: MD
authors.lastname: Greenhalgh
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors.forename: Charlene
authors.initials: C
authors.lastname: Fallan
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D000588:Amines / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D005663:Furans / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000588:Amines; D001572:Benzofurans; D005663:Furans; D007659:Ketones; D012997:Solvents; C018674:tetrahydrofuran; C043168:coumaran; D013890:Thiourea