4.8 Article

syn-Selective Catalytic Asymmetric 1,4-Addition of α-Ketoanilides to Nitroalkenes under Dinuclear Nickel Catalysis

Journal

ORGANIC LETTERS
Volume 12, Issue 14, Pages 3246-3249

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol101185p

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Funding

  1. Takeda Science foundation
  2. JSPS

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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.

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