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Catalytic Asymmetric Henry Reaction of Nitroalkanes and Aldehydes Catalyzed by a Chiral N,N-Dioxide/Cu(I) Complex

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journal contribution
posted on 20.02.2015 by Hongjiang Mei, Xiao Xiao, Xiaohu Zhao, Bing Fang, Xiaohua Liu, Lili Lin, Xiaoming Feng
An easily available N,N′-dioxide/Cu­(I) complex has been developed for the catalytic asymmetric nitroaldol (Henry) reaction of aldehydes with nitroethane. Under mild reaction conditions, a series of substituted aromatic, heteroaromatic and α,β-unsaturated aldehydes are transformed to the corresponding anti-β-nitroalcohols in good to excellent yields (up to 99%) with moderate to good dr (up to 16.7:1 anti/syn) and high ee values (up to 97%). Besides nitroethane, nitromethane and 1-nitropropane were also employed as nucleophiles, and good enantioselectivities were obtained.