A bench-stable homodinuclear Ni2-Schiff base complex for catalytic asymmetric synthesis of α-tetrasubstituted anti-α,β- diamino acid surrogates

Zhihua Chen, Hiroyuki Morimoto, Shigeki Matsunaga, Masakatsu Shibasaki

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271 Citations (Scopus)

Abstract

Catalytic asymmetric direct Mannich-type reactions of α-substituted nitroacetates using a new bench-stable homodinuclear Ni2-Schiff base 1b complex are described. The Ni2-1b complex gave Mannich products, precursors for anti-α,β-diamino acids with an α-tetrasubstituted carbon stereocenter, in >99-91% ee. The Ni2-1b complex was also applicable to direct Mannich-type reactions of malonates and β-keto ester, giving products in high stereoselectivity (up to 99% ee, dr >97:3). Preliminary mechanistic studies suggested that the dinuclear Ni metal centers had key roles to achieve good reactivity and high stereoselectivity.

Original languageEnglish
Pages (from-to)2170-2171
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number7
DOIs
Publication statusPublished - Feb 20 2008
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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