Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
Beilstein J Org Chem. 2014 Apr 17;10:883-9. doi: 10.3762/bjoc.10.85. eCollection 2014.
The Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates. Homologous aldehydes obtained from the vinyl group reacted in a typical way which led to α-hydroxyphosphonates, first reported compounds containing a direct P-C bond between the quinine carbon skeleton and a phosphorus atom. For the C9 ketones a phosphonate-phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced.
阿布拉莫夫反应是一种亲核加成反应，其中二烷基 H-膦酸酯（亚磷酸酯）在羰基化合物的作用下发生反应。氧化奎宁衍生物作为底物进行了反应。来自乙烯基的同系醛以典型的方式反应，生成α-羟基膦酸酯，这是首次报道的在奎宁碳骨架和磷原子之间含有直接 P-C 键的化合物。对于 C9 酮，证据表明存在膦酸酯-磷酸酯重排，以及哌啶片段的串联消除。
