H. Tavakol and S. Zakery, In Situ Addition of Organomethalic Reagents to Oxime Ethers, 40^th IUPAC congress, Beijing, china, 14-19 August 2005, Oral presentation

Abstract:

The addition of organomethalic nucleophiles to a carbon-nitrogen Oxime double bond has become an extremely useful process for the synthesis of a variety of Hydroxylamines¹. Some factors, which often diminish the versatility of these reactions, are poor electrophilicity of Oxime SP² Carbon, the liability of the nitrogen-oxygen bond, enolization of substrates with alpha-hydrogen, attack to Nitrogen versus Carbon, and the formation of side products such as Ketones², Amides³, Amines⁴, Nitriles³, Aziridines⁵, Amino Alcohols⁶, and Imines⁷. As a result, the innovation of new methods that can be led to one of these products (in most case, the favorite product is direct attack to only Oxime SP² carbon) in high yield without formation of side-products is very important in organic synthesis. In this paper, we wish to report the simple and easy addition of Allyl Tributyl Stananne , and ketene acetal to aromatic and aliphatic Aldehyde, respectively, in high yield (scheme 1).