A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered alpha-carbon atom of an alpha-hydroxyphosphonate

作者：Kiss Nora Zsuzsa; Kaszas Anna; Drahos Laszlo; Mucsi Zoltan; Keglevich Gyoergy^*

来源：Tetrahedron Letters, 2012, 53(2): 207-209.

DOI：10.1016/j.tetlet.2011.11.026

• alpha-Hydroxyphosphonate
• alpha-Aminophosphonate
• Nucleophilic substitution
• Microwave
• Neighbouring group effect

Diethyl alpha-hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 degrees C to afford the corresponding alpha-aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising ease due to the neighbouring group effect of the P=O moiety as was justified by DFT calculations carried out to evaluate the mechanism of the substitution under discussion.

• 出版日期2012-1-11