title: Highly diastereoselective synthesis of trans-2,5-disubstituted tetrahydrofurans.
abstract: trans-2,5-Disubstituted tetrahydrofurans were obtained as major diastereomers (trans/cis ratio 90:10-100:0) when acetylated gamma-lactols derived from (S)-glutamic acid were treated with titanium enolates of N-acetyl (R)-oxazolidin-2-thiones. A simple transesterification allowed us to obtain the corresponding methyl esters and recover the chiral auxiliary.
authors.affiliation: Laboratoire de Pharmacognosie, associé au CNRS (BioCIS), Université Paris-Sud, Faculté de Pharmacie, 5 rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Gaël
authors.initials: G
authors.lastname: Jalce
authors.forename: Matar
authors.initials: M
authors.lastname: Seck
authors.forename: Xavier
authors.initials: X
authors.lastname: Franck
authors.forename: Reynald
authors.initials: R
authors.lastname: Hocquemiller
authors.forename: Bruno
authors.initials: B
authors.lastname: Figadère
mesh_terms: D000107:Acetylation; D004951:Esterification; D005663:Furans / Q000138:chemical synthesis*; D018698:Glutamic Acid / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
chemical_list: D005663:Furans; D007783:Lactones; D009942:Organometallic Compounds; D023303:Oxazolidinones; D018698:Glutamic Acid; D014025:Titanium