Synthesis 2014; 46(15): 2079-2084
DOI: 10.1055/s-0033-1341064
paper
© Georg Thieme Verlag Stuttgart · New York

A One-Pot, Three-Step Synthesis of α-Aminophosphonic Acids

Sergey V. Ryabukhin*
a   The Institute of High Technologies, Kyiv National Taras Shevchenko University, 4 Glushkov str., Building 5, Kyiv 03187, Ukraine   Fax: +38(050)6424763   eMail: s.v.ryabukhin@gmail.com
b   Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska str., Kyiv 01601, Ukraine
,
Dmitriy M. Panov
b   Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska str., Kyiv 01601, Ukraine
,
Alexander N. Shivanyuk
a   The Institute of High Technologies, Kyiv National Taras Shevchenko University, 4 Glushkov str., Building 5, Kyiv 03187, Ukraine   Fax: +38(050)6424763   eMail: s.v.ryabukhin@gmail.com
,
Andrey S. Plaskon
b   Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska str., Kyiv 01601, Ukraine
,
Evgeniy N. Zarudnitskiy
c   Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska str., Kyiv 02094, Ukraine
,
Oleg Lukin
d   Curplyx DRS, JSC Macrochem 7th Floor, KOMOD Business Center, 4 Lunacharski str., Kyiv 02002, Ukraine
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 05. Februar 2014

Accepted after revision: 06. März 2014

Publikationsdatum:
11. April 2014 (online)


Abstract

A total of 20 α-aminophosphonic acids are synthesized in 73–89% yields via a one-pot, three-step procedure involving chlorotrimethylsilane-promoted condensation of carbonyl compounds and primary amines yielding azomethine intermediates, subsequent reaction with tris(trimethylsilyl) phosphite to give the corresponding trimethylsilylphosphonic esters and finally, mild cleavage with methanol–water. The wide scope and simple set-up and work-up procedures of the reported method allow the synthesis of a diverse set of α-aminophosphonic acids possessing two different functional groups.

Supporting Information