Organocatalytic enantioselective strecker reaction of imines containing a thiazole moiety by using a cinchona-based squaramide catalyst

Hai Xiao He, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

An organocatalytic enantioselective Strecker reaction was developed for the synthesis of α-amino nitriles that contain a thiazole moiety by using a cinchona-based squaramide catalyst. The corresponding products were obtained in good to excellent yields (up to 99%) with excellent enantioselectivities (up to 98% ee) by starting from aromatic-substituted imines. In addition, two trifunctional squaramides with amino acid residues were synthesized, and good enantioselectivities (up to 89% ee) were achieved when they were employed in the model reaction.

Original languageEnglish
Pages (from-to)6190-6199
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number28
DOIs
Publication statusPublished - Oct 2014

Keywords

  • Asymmetric catalysis
  • Enantioselectivity
  • Nitrogen heterocycles
  • Organocatalysis
  • Schiff bases
  • Synthetic methods

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