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Highly enantioselective reactions of configurationally labile epimeric diamine complexes of lithiated S-benzyl thiocarbamates.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Lange, Heiko Bergander, Klaus Fröhlich, Roland Kehr, Seda Nakamura, Shuichi Shibata, Norio Toru, Takeshi Hoppe, Dieter |
| Copyright Year | 2008 |
| Abstract | Substitution reactions that employ primary-carbamoyl-protected arylmethanethiols are described. The enantiodetermining step was found to occur in the post-deprotonation step as a dynamic thermodynamic resolution with a chiral bis(oxazoline) ligand. The configurationally labile lithium complexes were trapped with various electrophiles to yield different substitution products in good to excellent yields and enantiomeric excesses. The absolute configurations of the substitution products were determined, and the stereochemical pathway of the substitution reaction was elucidated for different classes of electrophiles. The temperature-dependent epimerization process was monitored by 1H and 6Li NMR spectroscopy. |
| Starting Page | 88 |
| Ending Page | 101 |
| Page Count | 14 |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | https://application.wiley-vch.de/contents/jc_2451/2008/f700262_s.pdf |
| PubMed reference number | 18067115v1 |
| Volume Number | 3 |
| Issue Number | 1 |
| Journal | Chemistry, an Asian journal |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | Addison Disease Class Diamine oxidase:ACnc:Pt:Ser/Plas:Qn Diamines Iron Overload Ligands Lithium Thermodynamics Thiocarbamates epimerization |
| Content Type | Text |
| Resource Type | Article |
