Highly enantioselective Henry (nitroaldol) reaction of aldehydes and alpha-ketoesters catalyzed by N,N'-dioxide-copper(I) complexes |
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Authors: | Qin Bo Xiao Xiao Liu Xiaohua Huang Jinglun Wen Yuehong Feng Xiaoming |
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Institution: | Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China. |
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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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