Abstract
Reaction of racemic biaryldicarboxylic dichloride with methyl 4, 6-O-benzylidene-α-D-glucopyranoside gave methyl 4, 6-O-benzylidene-2, 3-O- [(R) -biaryldicarbonyl] -α-D-glucopyranoside with perfect diastereoselection. This reaction provided a new method of optical resolution of axially- and planar chiral dicarboxylates. Using the methodology, several 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 α-D-glucose and their catalytic property for the asymmetric Michael addition has been investigated; enantioselectivity switching which is dependent on the azacrown ether catalysts has been achieved.
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