Highly diastereoselective synthesis of trans-2,5-disubstituted tetrahydrofurans.
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.
Jalce
Gaël
G
Laboratoire de Pharmacognosie, associé au CNRS (BioCIS), Université Paris-Sud, Faculté de Pharmacie, 5 rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
Seck
Matar
M
Franck
Xavier
X
Hocquemiller
Reynald
R
Figadère
Bruno
B
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
D005663:Furans; D007783:Lactones; D009942:Organometallic Compounds; D023303:Oxazolidinones; D018698:Glutamic Acid; D014025:Titanium