Catalytic Asymmetric Henry Reaction of Nitroalkanes and Aldehydes Catalyzed by a Chiral N,N′-Dioxide/Cu(I) Complex
2015
Mei, Hongjiang | Xiao, Xiao | Zhao, Xiaohu | Fang, Bing | Liu, Xiaohua | Lin, Lili | Feng, Xiaoming
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.
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