Albumin-mediated asymmetric nitroaldol reaction of aromatic aldehydes with nitromethane in water

作者：Matsumoto Kazutsugu^*; Asakura Shota

来源：Tetrahedron Letters, 2014, 55(50): 6919-6921.

DOI：10.1016/j.tetlet.2014.10.109

• Aqueous media
• Asymmetric nitroaldol reaction
• Biocatalysis
• Human serum albumin
• Optically active nitro alcohols

We succeeded in the asymmetric nitroaldol (Henry) reaction of aromatic aldehydes with nitromethane using human serum albumin (HSA) in water at neutral pH. The reaction of 4-nitrobenzaldehyde smoothly proceeded for 24 h at 30 degrees C to afford the corresponding (R)-2-nitro-1-(4-nitrophenyl)ethanol (27% ee). Lowering the reaction temperature to 0 degrees C improved the enantioselectivity (53% ee). Although the denatured HSA also catalyzed the coupling reaction, no enantioselectivity was observed. The reaction was also applicable to other substrates bearing various substitutions on the benzene ring, and the ee of (R)-1-(biphenyl-4-yl)-2-nitroethanol was up to 79% ee.

• 出版日期2014-12-10