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  • Title: Highly enantioselective Henry (nitroaldol) reaction of aldehydes and alpha-ketoesters catalyzed by N,N'-dioxide-copper(I) complexes.
    Author: Qin B, Xiao X, Liu X, Huang J, Wen Y, Feng X.
    Journal: J Org Chem; 2007 Nov 23; 72(24):9323-8. PubMed ID: 17973533.
    Abstract:
    A new chiral N,N'-dioxide-Cu(I) catalyst has been developed for the asymmetric Henry (nitroaldol) reaction. The approach benefited from the easy modification of the chiral space. As the highly effective N-oxide ligand, 1d has been adopted for the Henry reaction with both aromatic and heteroaromatic aldehydes. The corresponding nitro-alcohol products were obtained in good yields with high enantiomeric excesses up to 98%. Moreover, alpha-ketoesters were also catalyzed by this catalyst to give attractive optically active alpha-hydroxy beta-nitro esters containing chiral quaternary carbon centers (up to 99% ee). On the basis of a combination of several techniques including the 1H NMR, ESI-HRMS, and MM2 calculations, the proposed mechanism was presented to explain the origin of reactivity and asymmetric inductivity.
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