188909-33-3

Upstream product

• 109-72-8 n-butyllithium 
• 188909-23-1 2-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone O-benzyl-oxime 
• 188909-26-4 2-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone O-benzyl-oxime 
• 147107-70-8 1-O-t-butyldiphenylsilyl-3,4-O-isopropylidene-L-erythrulose 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 

Downstream Products

• 211044-92-7 (2R,3R)-3,4-O-isopropylidene-2-(N-benzyloxyamino)-2-n-butylbutane-1,3,4-triol 

Relevant academic research and scientific papers

Diastereoselectivity of the reactions of organolithium reagents with protected erythrulose oximes

The addition of organolithium reagents to the C=N bond of several erythrulose-derived chiral (E)- and (Z)-ketoxime ethers has been shown to be highly diastereoselective in the case of the (E)-isomers. Chelated and nonchelated transition states have been proposed to rationalize these results, with additional support of computational methods.

Diastereoselective additions of organolithium reagents to the C=N bond of protected erythrulose oxime ethers. Synthesis of enantiopure α,α-disubstituted α-aminoacids

The addition of organolithium reagents to the C=N bond of several erythrulose-derived chiral (E)- and (Z)-ketoxime ethers has been shown to be highly diastereoselective for the (E)-isomers. A chelated transition state has been proposed to explain this result. The addition products were converted into the two α,α-disubstituted α-aminoacids (R)-2-(-)-methylserine and (R)-(+)-2-phenylserine.