Two-fold modification of the phenyl substituent in phenylphosphonic acid monoester monoamides

J Org Chem. 2012 Sep 21;77(18):8244-56. doi: 10.1021/jo301526k. Epub 2012 Sep 7.


Phenylphosphonic acid ethyl ester N,N-diethylamide was subjected to a double modification of its phenyl substituent through directed ortho-metalation followed by dearomatization of the aryl substituent under Birch reduction conditions. Application of the same methodology to a diastereomerically pure phenylphosphonic acid monoester monoamide led to the formation of P-stereogenic cyclohexadienyl-phosphonic acid derivatives. The method offers a simple and efficient modification of phenyl substituent in organophosphorus compounds.