Abstract
Eight new pinene based tridentate Schiff bases of (+)-(1S,2R,3S,5S)-3-amino-6,6-dimethylbicyclo[3.1.1]heptan-2-ol were synthesized from (+)-(α)-pinene. Copper complexes of these Schiff bases were prepared for asymmetric nitroaldol (Henry) reaction. Among the eight copper complexes, 3-methylsalicylaldehyde-derived [CuSBADBH-4]2 32 showed high chiral induction (85 % ee) for the catalytic asymmetric Henry reaction of 4-nitrobenzaldehyde. Under optimal reaction conditions, 1 mol% [CuSBADBH-4]2 32 catalyzed enantioselective Henry reaction of various aromatic and poly aromatic aldehydes afforded the corresponding (R)-β-hydroxy nitroalkanes with high ee (up to 92 %) and yield (up to 99 %).
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