Synthesis and application of new iminopyridine ligands to enantioselective copper(II)-catalyzed Henry reaction

• New chiral iminopyridines were obtained from pyridyl aldehydes or ketones.
• New chiral iminopyridines were obtained from a variety of chiral amines.
• New chiral iminopyridines were assessed in the enantioselective Henry reaction.
• 1-(2-Methoxyphenyl)-2-nitroethanol was formed with enantioselectivities up to 82% ee.

Chiral iminopyridines obtained by reaction between a variety of chiral amines and pyridyl aldehydes or ketones were assessed as catalysts in the enantioselective Henry reaction between nitromethane and 2-methoxybenzaldehyde in the presence of copper(II) acetate. 1-(2-Methoxyphenyl)-2-nitroethanol was obtained in moderate yields and good enantioselectivities (up to 82% ee) under straightforward experimental conditions without the need for air or moisture exclusion. The best enantioselectivity (82% ee) was obtained by an iminopyridine based on a camphane skeleton.

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