Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines

Qihang Shao, Liang Wu, Jianzhong Chen, Ilya D. Gridnev, Guoqiang Yang, Fang Xie, Wanbin Zhang

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A Cu(II)/RuPHOX-catalyzed enantioselective Mannich-type reaction of glycine Schiff bases with cyclic ketimines was developed, affording chiral α,ß-diamino acid derivatives in good yields with moderate to good ee and dr values. This provides an efficient methodology for furnishing chiral Cβ-tetrasubstituted α,β-diamino acid precursors. The catalytic system is compatible with a series of substrates. In addition, an interesting nonlinear effect of the catalyst's enantiomeric composition on reaction enantioselectivity was observed. (Figure presented.).

Original languageEnglish
Pages (from-to)4625-4633
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number23
DOIs
Publication statusPublished - 2018 Dec 3

Keywords

  • Cu
  • Mannich-type reaction
  • RuPHOX
  • asymmetric catalytic
  • cyclic ketimines

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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