104322-41-0Relevant articles and documents
Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides
Rehnberg, Nicola,Magnusson, Goeran
, p. 5467 - 5476 (2007/10/02)
The chiral aldehydes (-)-(2S,5S)- and (-)-(2S,5R)-2-oxy>methyl>-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15percent yield, respectively, by lithium bromide induced rearrangement of 6-O-silylated methyl 2,3- and 3,4-anhydro-α- and -β-D-hexopyranosides, obtained in two steps from methyl α- and β-D-glucopyranoside.Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes.Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.
ASYMMETRIC DIELS-ALDER REACTION BETWEEN THE CHIRAL ISOPRENE UNITS 2-(R)-AND (S)-BENZYLOXY-2,5-DIHYDRO-4-FURANCARBOXALDEHYDE AND CYCLOPENTADIENE
Sundin, Anders,Frejd, Torbjoern,Magnusson, Goeran
, p. 5605 - 5608 (2007/10/02)
The title Diels-Alder reaction gave a mixture of enantiomerically pure adducts with complete norbornane-type monoterpene skeletons.The exo/endo ratio of the products changed from approximately 4:1 at 5 deg to 2:1 at 165 deg.