syn-Selective catalytic asymmetric 1,4-addition of alpha-ketoanilides to nitroalkenes under dinuclear nickel catalysis.
A syn-selective catalytic asymmetric 1,4-addition of alpha-ketoanilides to nitroalkenes is described. The homodinuclear Ni(2)-Schiff base 1b complex was suitable for the reaction, and products were obtained in 61-92% yield, 8.3:1 --> 20:1 syn-selectivity, and 72-98% ee. Stereoselective transformation of the 1,4-adduct to a trisubstituted pyrrolidine was also performed.
Xu
Yingjie
Y
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000475:Alkenes / Q000737:chemistry*; D000813:Anilides / Q000737:chemistry*; D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D000813:Anilides; D009532:Nickel