General and practical catalytic enantioselective Strecker reaction of ketoimines: Significant improvement through catalyst tuning by protic additives

Nobuki Kato, Masato Suzuki, Motomu Kanai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

110 Citations (Scopus)

Abstract

Significant improvement in enantioselectivity and catalyst activity was achieved for the catalytic enantioselective Strecker reaction. Using a catalyst (1-2.5mol%) prepared from Gd(OiPr)3 and D-glucose derived ligand 1, and in the presence of 2,6-dimethylphenol as an additive, high enantioselectivity was obtained from a wide range of ketoimines, including heteroaromatic and cyclic ketoimines. The new method was applied to an efficient catalytic asymmetric synthesis of sorbinil, a therapeutic agent for diabetic complications.

Original languageEnglish
Pages (from-to)3147-3151
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number15
DOIs
Publication statusPublished - 2004 Apr 5
Externally publishedYes

Keywords

  • Additive effect
  • Asymmetric catalysis
  • Disubstituted amino acids
  • Ketoimines
  • Strecker reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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