Scientific Reports (Jan 2018)

Dinuclear PhosphoiminoBINOL-Pd Container for Malononitrile: Catalytic Asymmetric Double Mannich Reaction for Chiral 1,3-Diamine Synthesis

  • Takayoshi Arai,
  • Katsuya Sato,
  • Ayu Nakamura,
  • Hiroki Makino,
  • Hyuma Masu

DOI
https://doi.org/10.1038/s41598-018-19178-4
Journal volume & issue
Vol. 8, no. 1
pp. 1 – 8

Abstract

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Abstract A phosphoiminoBINOL ligand was designed to form a dinuclear metal complex that could hold a malononitrile molecule. The dinuclear bis(phosphoimino)binaphthoxy-Pd2(OAc)2 complex catalyzed a double Mannich reaction of N-Boc-imines with malononitrile to give chiral 1,3-diamines with high enantioselectivity. The rational asymmetric catalyst, which smoothly introduces the first coupling product to the second coupling reaction while avoiding the reverse reaction, facilitates the over-reaction into a productive reaction process.