H. Tavakol and A. Heydari, One-Pot Synthesis of   Substituted Hydroxylamines Using LPDE 5M, XVIIIth Turkish National Congress, Kafkas University, Kars, Turkey, 6-9 July 2004

Abstract

The addition of nucleophiles to a carbon-nitrogen double bond has become an extremely useful process for the synthesis of a variety of amines, a-amino acids, a-aminophosphonates and other compounds of interest.¹ Typically organometallic reagents can be utilized to achieve this carbon-carbon bond forming reaction.² Recently, we have demonstrated the synthetic utility of lithium perchlorate/ diethyl ether (LPDE) solution (1.0 – 5.0 M) in the preparation of several nitrogen-containing compounds.³ We have focused our attention on the use of LPDE medium for oximes activation. In summary, three-component reactions between aldehydes, O-trimethylsilyl hydroxylamine, and nucleophiles have been successfully carried out by using LPDE solution to afford a-substituted hydroxylamine derivatives in high yields (see bellow) . The reactions are very clean and the procedure is very easy; simple mixing almost equimolar amounts of an aldehyde, O-trimethylsilyl hydroxylamine, and nucleophile.