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

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.

Citation

Marek Stankevič, Jolanta Bazan. Two-fold modification of the phenyl substituent in phenylphosphonic acid monoester monoamides. The Journal of organic chemistry. 2012 Sep 21;77(18):8244-56

PMID: 22931119

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