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Regiospecific and highly stereoselective synthesis of β-amino (Z)-enylphosphonates via β-hydrogen migration reaction of dialkyl α-diazophosphonates catalyzed by AgOTf
| Content Provider | Semantic Scholar |
|---|---|
| Author | Ge, Haihong Yu, Chengbin Sun, Weize Zhan, Junchen Miao, Zhiwei |
| Copyright Year | 2014 |
| Abstract | A series of dialkyl α-diazophosphonates bearing different substituents have been prepared from natural amino acids in order to investigate the steric effect in 1,2-migration reaction of metal carbenes. The diazo decomposition of the diazophosphonates using the AgOTf/NaBArF complex resulted in β-hydrogen migration to give β-amino (Z)-enylphosphonates in good yields with high regio- and stereoselectivity. A possible reaction mechanism shows that the steric effect could dramatically influence the geometric isomerism aptitude. This new method for constructing (Z)-β-amino vinylphosphonates should be of general utility in organic synthesis. |
| Starting Page | 21492 |
| Ending Page | 21496 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/C4RA02520B |
| Volume Number | 4 |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/getauthorversionpdf/C4RA02520B |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/ra/c4/c4ra02520b/c4ra02520b1.pdf |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |