Development of asymmetric reactions using a glucose-scaffold

摘要

Reaction of recemic biaryldicarboxylic dichloride with methyl 4,6-O-benzlidene-#alpha#-D-glucopy-ranoside gave methyl 4,6-O-benzylidene-2,3-O-[(R)-biaryldicarbonyl]-#alpha#-D-glucopyranoside with perfect diastereoselection.This reactiion provided a new method of optical resolution of axially- and planar chiral dicarboxylates.Using the methodology,swveral types of novel ferrocenyl sugars which showed anti-malaria parasite (P.falciparum)activity have been prepared.Ten types of chiral azacrown ethers were synthesized from #alpha#-D-glucose and their catalytic property for the asymmetric Michael addition has been investigated;enantioselectivity swwitching which is dependent on the azacrown ether catalysts has been achieved.