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LETTERSynlett 2003: 2321-2324  
DOI: 10.1055/s-2003-42118

© Georg Thieme Verlag Stuttgart · New York

 

A Novel Catalytic Three-Component Synthesis (Kabachnick-Fields Reaction) of α-Aminophosphonates from Ketones
 
Elena D. Matveeva*, Tatyana A. Podrugina, Elena V. Tishkovskaya, Larisa G. Tomilova, Nikolay S. Zefirov*
Department of Chemistry, Moscow Lomonosov University, Moscow, Russia
Fax: +7(95)9390290; e-Mail: edmatveeva@mail.ru; e-Mail: zefirov@org.chem.msu.ru;
Received 11 July 2003

Abstract

A novel and highly convenient catalytic variant of the synthesis of α-aminophosphonates on basis of the Kabachnik-Fields reaction [three-component reaction of ketones, diethylphosphite and either benzylamine (series a) of ammonium carbonate (series b)] in the presence of tetra-tert-butylphthalocyanines has been developed. This method affords α-aminophosphonates in acceptable yields for various ketones, including cyclic, sterically hindered and cage ketones. The unsubstituted α-aminophosphonic acids were also obtained from the corresponding esters of series b.

Key words

α-aminophosphonates - catalysis - tetra-tert-butyl­phthalocyanines - ketones - α-aminophosphonic acids

 
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