H. Tavakol, Synthesis of α-hydroxy amino phosphonates from aldehydes  XVII EuCheMS Conference on Organometallic Chemistry, Sofia, Bulgaria, 1-6 September 2007

Abstract

Addition of phosphorus nucleophiles to C=O double bond is a known method for preparation of organic compounds containing phosphorus atom. Also, addition of phosphorus nucleophiles to C=N double bond is very good procedure for preparation of some important compound with application in scientific and drug synthesis such as α-hydroxy amino phosphonates that they show similar activity to a-hydroxy amino alkyl carboxylic acids and a-hydroxy amino alkyl phosphonic acids and their derivatives in strong antibacterial activity¹. By reviewing literatures, only a few examples of the synthesis of a-hydroxy amino phosphonates or similar compounds have been reported^2-4. Unfortunately, these methods are limited by a narrow scope, by competition with other reactions, and difficulties in the preparation of the starting materials. But we succeeded at preparing these compounds by using simple and easy method and commercially available compounds that in this paper we reported this procedure.

In our researches, we first succeed at in situ preparation of oxime ethers from condensation reaction between aldehydes and O-trimethylsilyl hydroxylamine, and then add nucleophiles to synthesized oxime ethers. Both two steps are carried out in one vessel and in presence of lithium perchlorate as a catalyst in diethyl ether solution (LPDE solution).. After work-up stage and purification of product by column chromatography, we obtain only α-hydroxy amino phosphonates as major product.