Simple and Effective Synthetic Approach to Chiral 2-Amino-4-piperidinyl Pyridine Derivatives

Abstract

A facile way has been developed to provide a series of novel chiral N-(4-(piperidin-1-yl)pyridin-2-yl)amide derivatives as potential stereoselective catalysts. The key intermediate, 2-amino-4-piperidinyl pyridine, was obtained by nucleophilic substitution of 2-amino-4-chloropyridine with piperidine in good yields (up to 96%). The total control of enantioselectivity was obtained for the synthesis of L-proline and (R)-1,1′-bi(2-naphthol) derivatives.

GRAPHICAL ABSTRACT

Keywords:

• 2-Amino-4-piperidinyl pyridine
• chiral catalysts
• DMAP
• PPY

ACKNOWLEDGMENTS

The authors thank the sophisticated instrumentation faculty at the department of analytical chemistry in Jilin University, Xu-Yang Luo for recording ¹H and ¹³C NMR spectra, and Qin-Wen Liu for recording the mass spectra.

Notes

^a Isolated yield after silica-gel column chromatography.

^b Reacted in an autoclave.