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Axially chiral Ni(II) complexes of α-amino acids: Separation of enantiomers and kinetics of racemization
| Content Provider | Hyper Articles en Ligne (HAL) |
|---|---|
| Author | Zhang, Wenzhong Ekomo, Romuald Eto Roussel, Christian Moriwaki, Hiroki Abe, Hidenori Jianlin, Han Soloshonok, Vadim A. |
| Abstract | Herein we present design, synthesis, chiral HPLC resolution, and kinetics of racemization of axially chiral Ni(II) complexes of glycine and di-(benzyl)glycine Schiff bases. We found that while the ortho-fluoro derivatives are configuration-ally unstable, the pure enantiomers of corresponding axially chiral ortho-chloro-containing complexes can be isolated by preparative HPLC and show exceptional configurational stability (t 1/2 from 4 to 216 centuries) at ambient conditions. Synthetic implications of this discovery for the development of new generation of axially chiral auxiliaries, useful for general asymmetric synthesis of α-amino acids, are discussed. |
| Ending Page | 508 |
| Page Count | 11 |
| Starting Page | 498 |
| File Format | |
| ISSN | 08990042 |
| e-ISSN | 1520636X |
| DOI | 10.1002/chir.22815 |
| Journal | Chirality |
| Issue Number | 4 |
| Volume Number | 30 |
| Language | English French |
| Publisher | Wiley |
| Publisher Date | 2018-04-01 |
| Access Restriction | Open |
| Subject Keyword | amino acids axial chirality chiral HPLC kinetic of racemization rotational energy barriers chim Chemical Sciences |
| Content Type | Text |
| Resource Type | Article |
| Subject | Spectroscopy Organic Chemistry Drug Discovery Analytical Chemistry Pharmacology Catalysis |
