445283-77-2

Upstream product

• 857293-94-8 (1R)-N-acetoxy-N-benzyl-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-1-methylethyl]amine 
• 857293-91-5 (1R)-N-benzyl-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-[1,3]dioxolan-4(R)-yl)-1-methylethyl]hydroxylamine 
• 857293-96-0 methyl (2R)-2-(N-acetoxy-N-benzylamino)-3-(tert-butyldiphenylsilyloxy)-2-methylpropionate 

Relevant academic research and scientific papers

Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose

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.

Synthesis of α,α-disubstituted α-amino acid derivatives in enantiopure form via stereoselective addition of Grignard reagents to a chiral acyclic nitrone derived from L-erythrulose

The additions of various Grignard reagents to a chiral nitrone prepared from L-erythrulose take 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 acidic additives: zinc bromide enhances attack to the si face whereas diethyl aluminum chloride promotes attack to the re side. The obtained adducts can be then efficiently transformed into protected N-hydroxy α,α-disubstituted α-amino acid derivatives as well as into the corresponding α,α-disubstituted α-amino acids.