1583285-59-9Relevant academic research and scientific papers
Regiospecific and highly stereoselective synthesis of β-amino (Z)-enylphosphonates via β-hydrogen migration reaction of dialkyl α-diazophosphonates catalyzed by AgOTf
Cai, Yan,Ge, Haihong,Yu, Chengbin,Sun, Weize,Zhan, Junchen,Miao, Zhiwei
, p. 21492 - 21496 (2014/06/10)
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. This journal is the Partner Organisations 2014.
Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2
Cai, Yan,Lyu, Hairong,Yu, Chengbin,Miao, Zhiwei
, p. 596 - 602 (2014/05/20)
A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.
