Asymmetry Henry Reaction Catalyzed by Camphor-based Chiral Ligands
| Autor: | Yu-Chan Chen, 陳玉嬋 |
|---|---|
| Rok vydání: | 2015 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 103 Optically active β-nitro alcohols, obtained by asymmetric Herny reaction of nitroalkane to aldehydes, can be further converted into various functional groups. They are important intermediate pharmaceuticals and natural products. Numerous chiral ligands derived from camphor had been developed and applied in the asymmetric additions to afford corresponding adducts in good yields and enantioselectivities. Therefore, we want to develop a series of new chiral ligands containing camphor skeleton and apply them in asymmetric Henry reaction. The new chiral ligands were combined with amino alcohol, prepared from camphor in three steps, and aziridines derived from natural amino acids. The asymmetric Henry reaction was carried out at room temperature. The chiral ligand was then used to coordinate with Cu(OAc)2‧H2O at room temperature, and the resulting complex was utilized to catalyze the addition reaction to different aldehydes under the same conditions. The optimum conditions were 2.5 mol% 1:1 metal and ligand in i-PrOH for 24‒72 h. The product was obtained in 7‒82% yield with 72‒86% ee. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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