Catalytic Asymmetric Henry Reaction of Nitroalkanes and Aldehydes Catalyzed by a Chiral N,N′-Dioxide/Cu(I) Complex
journal contributionposted on 20.02.2015 by Hongjiang Mei, Xiao Xiao, Xiaohu Zhao, Bing Fang, Xiaohua Liu, Lili Lin, Xiaoming Feng
Any type of content formally published in an academic journal, usually following a peer-review process.
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.