Synthesis of chiral pyridino-15-crown-5 type ligands containing α-D-hexapyranoside unit and their application in asymmetric synthesis

Abstract

The synthesis of novel chiral monoaza-15-crown-5 compounds (1-4) with pyridine-ring starting from methyl-4,6-O-benzylidene-α-D-glucopyranoside and methyl-4,6-O-benzylidene-α-D-mannopyranoside by different methods are reported. These crown ethers showed significant asymmetric induction in a Michael addition (up to 80% ee).