Synthesis and applications in Henry reactions of novel chiral thiazoline tridentate ligands

Ye Shi, Yang Li, Jingbo Sun, Qi Lai, Chiyu Wei, Zhiyong Gong, Qiang Gu, Zhiguang Song*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Several novel chiral tridentate ligands containing thiazoline were efficiently synthesized from commercially available l=cysteine in high yield. These ligands were subsequently applied to the asymmetric Henry reaction of nitromethane and various aldehydes. It was found that the structures of the thiazoline ligands had a significant influence on the enantioselectivity. It was shown that the optimal catalyst for this reaction was a ligand complexed with CuCl, which was formed from chiral thiazoline with chiral aminoalcohol. At -20°C, with 10 mol% of this ligand, a product with (S)-configuration was isolated in 93% yield and 98% enantiomeric excess.

Original languageEnglish
Pages (from-to)661-667
Number of pages7
JournalApplied Organometallic Chemistry
Volume29
Issue number10
DOIs
Publication statusPublished - 1 Oct 2015
Externally publishedYes

Keywords

  • Henry reactions
  • asymmetric synthesis
  • chiral thiazoline ligand

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