title: Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene O-H Insertion Reaction.
abstract: Copper- or rhodium-catalyzed reactions of diazocarbonyl compounds with β-hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single-step process starts as a carbene O-H insertion reaction, but is diverted by an intramolecular aldol reaction.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).
authors.forename: Simon M
authors.initials: SM
authors.lastname: Nicolle
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).
authors.forename: William
authors.initials: W
authors.lastname: Lewis
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Hayes
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK). c.j.moody@nottingham.ac.uk.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moody
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; C030011:carbene; D003300:Copper; D012238:Rhodium; D008697:Methane
keywords: aldol reaction; carbenes; diazo compounds; tetrahydrofurans; transition-metal catalysis