Yao Qian, Wang Zhen, Zhang Yuheng, Liu Xiaohua, Lin Lili, Feng Xiaoming
‡Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, People's Republic of China.
J Org Chem. 2015 Jun 5;80(11):5704-12. doi: 10.1021/acs.joc.5b00649. Epub 2015 May 13.
A highly efficient N,N'-dioxide/Gd(III) complex has been developed for the enantioselective conjugate addition of nitroalkanes to α,β-unsaturated pyrazolamides. Under mild reaction conditions, a series of γ-nitropyrazolamides were obtained in good to excellent yields (up to 99%) with excellent enantioselectivities (up to 99% ee). What's more, the optically active products could be easily transformed into γ-nitroesters which were key intermediates for the preparation of paroxetine, pregabalin and boclofen.
