866925-83-9Relevant academic research and scientific papers
Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose
Murga, Juan,Portoles, Raul,Falomir, Eva,Carda, Miguel,Marco, J. Alberto
, p. 1807 - 1816 (2007/10/03)
The additions of various organolithium and organomagnesium reagents to a chiral nitrone prepared from L-erythrulose took place with variable diastereoselectivity. The degree and strength of the facial selectivity can be modified if the reaction is performed in the presence of Lewis acid additives: zinc bromide enhances the attack to the Si face of the C=N bond whereas diethyl aluminium chloride promotes attack to the Re face. The obtained adducts can be then transformed into protected N-hydroxy-α,α-disubstituted-α- amino acid derivatives as well as into the corresponding α,α- disubstituted α-amino acids.
