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Paper | Regular issue | Vol 87, No. 4, 2013, pp.815-826
Published online, 20th February, 2013
DOI: 10.3987/COM-12-12661
Synthesis of Nitrogen Bridgehead Heterocycles with Phosphonates via a Novel Tandem Process

Ya-Fei Xie, Yan-Qing Ge, Lei Feng, Hua-Qiang Xu, Song Meng, Gui-Long Zhao, Wei-Ren Xu, Jiong Jia,* and Jian-Wu Wang*

*School of Chemistry and Chemical Engineering, Shandong University, 27 Shanda Nanlu, Jinan,Shandong, 250100, China


A novel and efficient method was developed for the synthesis of nitrogen bridgehead heterocycles with phosphonates. Nitrogen containing five-membered heterocyclic aldehyde and diethy 3-bromoprop-1-enylphosphonate were used as substrates. Bridgehead nitrogen-containing arylphosphonates were obtained via one-pot reaction including four steps: SN2, deprotonation followed by electron flow, nucleophic additon and elimination of water.