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1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
| Content Provider | Semantic Scholar |
|---|---|
| Author | Ge, Haihong Liu, Shuang Sun, Yuchao Miao, Zhiwei |
| Copyright Year | 2015 |
| Abstract | The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino ( E )-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN) 4 PF 6 ] as the catalyst and N , N -dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E / Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino ( E )-enylphosphonates in moderate to good yields. |
| Starting Page | 448 |
| Ending Page | 454 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1055/s-0035-1560373 |
| Volume Number | 48 |
| Alternate Webpage(s) | https://www.thieme-connect.com/media/synthesis/201603/supmat/sup_ss-2015-h0450-op_10-1055_s-0035-1560373.pdf |
| Alternate Webpage(s) | https://doi.org/10.1055/s-0035-1560373 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
