208515-22-4

Upstream product

• 309297-56-1 erythrulose 3,4-acetonide E/Z oxime 
• 115114-86-8 3,4-O-isopropylidene-L-(S)-erythrulose 
• 591-51-5 phenyllithium 
• 208515-19-9 (R)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-2,5-dihydro-1,3-oxazole N-oxide 
• 100-58-3 phenylmagnesium bromide 

Relevant academic research and scientific papers

Diastereoselective additions of organolithium and organomagnesium reagents to the C=N bond of a chiral, cyclic nitrone derived from erythrulose

The reaction of the 3,4-O-isopropylidene-L-(S)-erythrulose with hydroxylamine, followed by treatment of the resulting mixture of (E)- and (Z)-oximes with acetone and an acid catalyst, afforded two crystalline chiral compounds. Through X-ray diffraction analysis, these products were identified as a double acetonide derived from the (E)-oxime and a cyclic nitrone derived from the (Z)-oxime. The additions of organolithium and organomagnesium reagents to the C=N bond of the nitrone were found to be diastereoselective. The addition products are useful intermediates for the preparation of α,α- disubstituted α-aminoacids and other nitrogen-containing compounds in enantiopure form.