Diastereoselective construction of a new class of nicotine analogues having contiguous stereocenters via 1,3-dipolar cycloaddition of azomethine ylides

Abstract

Diastereoselective synthesis of several nicotine analogues via the intermolecular cycloaddition of azomethine ylides derived from the condensation reaction of nicotinaldehyde/ picolinaldehyde/ isonicotinaldehyde and N-methyl glycine/N-benzyl glycine hydrochloride with several readily available electron-deficient 2p components, (maleimides, dialkyl fumarates, dialkyl maleates and fumaronitrile) is reported. The assembling of a new class of nicotine analogues/ functionalized 2-pyridylpyrrolidine derivatives having contiguous stereocenters has been accomplished. The stereochemistry of the representative products is unequivocally established from the single crystal X-ray structure analyses.