Catalytic anti-selective asymmetric Henry (nitroaldol) reaction catalyzed by Cu(I)–amine–imine complexes

Chiral complex derived from N-methyl-C1-tetrahydro-1,1′-bisisoquinolines (R)-1b and Cu(I)Cl promoted the diastereoselective Henry reaction of nitroethane with a series of aromatic and aliphatic aldehydes. The nitroalcohol adducts were obtained in excellent yields (up to 95%), moderate anti-selectivity (up to 2.6:1), and good enantioselectivity (up to 92% ee) without any special precautions to exclude moisture or air.

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(R)-N′-Methyl-1′,2′,3′,4′-tetrahydro-1,1′-bisisoquinolineC19H18N2[α]D25=+159.7 (c 1.13, CH2Cl2)Source of chirality: resolutionAbsolute configuration: (R)