Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate-phosphate rearrangement and tandem intramolecular piperidine elimination

作者：Gorecki Lukasz; Mucha Artur; Kafarski Pawel^*

来源：Beilstein Journal of Organic Chemistry, 2014, 10: 883-889.

DOI：10.3762/bjoc.10.85

• carbonyl derivatives
• dialkyl phosphite addition
• organophosporus
• phosphonate-phosphate rearrangement
• quinine oxidation

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 alpha-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.

• 出版日期2014-4-17