420810-52-2Relevant academic research and scientific papers
Investigation of the transition-metal- and acid-catalyzed reactions of β-(N-tosyl)amino diazo carbonyl compounds
Jiang, Nan,Ma, Zhihua,Qu, Zhaohui,Xing, Xiaoyu,Xie, Linfeng,Wang, Jianbo
, p. 893 - 900 (2007/10/03)
A series of β-(N-tosyl)amino diazo carbonyl compounds have been prepared by nucleophilic condensation of N-tosylimines with acyldiazomethanes. The diazo decomposition of these diazo carbonyl compounds under various catalytic conditions, including Rh(II) carboxylates, Cu(I) and Cu(II) complexes, PhCO2Ag/Et3N, TsOH, and SnCl2·2H2O, has been investigated. It was found that, in most cases, the diazo decomposition gave preferentially 1,2-aryl migration product, but 1,2-hydride migration predominated when PhCO2Ag/Et3N was the catalytic system. Hammett correlation has been applied in the analysis of the electronic effects of 1,2-aryl migration. The factors that govern the migratory preference and the mechanistic aspects of the reaction are discussed.
An efficient approach to α-aryl β-amino esters through 1,2-aryl migration of p-toluenesulfonic acid mediated diazo decomposition
Jiang,Wang
, p. 149 - 151 (2007/10/03)
A new method for the synthesis of α-aryl β-amino esters has been developed. The key step in this preparation is the chemoselective 1,2-aryl migration of diazo carbonyl compounds catalyzed by TsOH.
