Asymmetric 1,4-additions to 5-alkoxy-2(5h)-furanones

Asymmetric 1, 4-additions to 5-alkoxy-2 (5H)-furanonesenantioselective synthesis and absolute configuration determination of β-amino-δ-butyrolactones and amino diols

“…In line with the observation of diastereofacial Diels-Alder reactions 18 and thiol additions 16 to 1 and stereocontrolled 1,4-additions to 5-tbutyloxymethyl-[5H]-furanone 10 , we expected that the amine additions to 1 would also preferentially proceed anti to the C5-menthyloxy substituent.…”

“…Watt high pressure mercury lamp (Hanau) analogous to procedures described before 16,17,35 , 2[5H]-furanone was prepared following the procedure described by Nasman and Pensar. 36 5-n-Butyl-2[5H]-furanone was prepared as described by…”

“…Enantiomerically pure butenolide 1 is readily available in gram quantities through a three step procedure from furfural as was described previously 16 (eq.2). Singlet oxygen photooxidation of furfural 17 followed by acetalization with l-menthol yields two diastereomeric l-menthyloxyfuranones.…”

Structure of (+)-(3S,4R,5R,1'R,2'S,5'R)-tetracarbonyl{(3,4-η2)-5-[5'-methyl-2'-(1-methylethyl)cyclohexyloxy]-2(5H)-furanone}iron

“…Reaction of iron enneacarbonyl with the easily available (-)-5-menthyloxy-2(5H)-furanone (1) (Feringa & de Lange, 1988) C.. F~(co),…”

New approaches in asymmetric synthesis using γ-alkoxybutenolides

“…The short synthetic route to both enantiomers of 3,4-epoxybutanol 14 illustrates only one of the various application of 4-sulfide substituted lactones 27.…”