Synthesis and applications in Henry reactions of novel chiral thiazoline tridentate ligands |
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| Authors: | Ye Shi Yang Li Jingbo Sun Qi Lai Chiyu Wei Zhiyong Gong Qiang Gu Zhiguang Song |
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| Affiliation: | 1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China;2. Department of Applied Chemistry, College of Chemistry, Jilin University, Changchun, China |
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| 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. Copyright © 2015 John Wiley & Sons, Ltd. |
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| Keywords: | chiral thiazoline ligand Henry reactions asymmetric synthesis |
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