188909-27-5

Upstream product

• 622-33-3 N-benzyloxyamine 
• 153096-71-0 (S)-3,4-Bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-one 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 

Downstream Products

• 188909-43-5 O-Benzyl-N-[(R)-1-((R)-1,2-bis-benzyloxy-ethyl)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl]-hydroxylamine 
• 188909-31-1 O-Benzyl-N-[(1R,2R)-2,3-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-propyl]-hydroxylamine 
• 188909-39-9 O-Benzyl-N-[(1R,2R)-2,3-bis-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-1-phenyl-propyl]-hydroxylamine 
• 211045-03-3 (2R,3R)-3,4-di-O-benzyl-2-(N-benzyloxyamino)-2-n-butylbutane-1,3,4-triol 
• 211045-05-5 (2R,3R)-3,4-O-di-O-benzyl-2-(N-benzyloxyamino)-2-allylbutane-1,3,4-triol 
• 211045-02-2 (2R,3R)-3,4-di-O-benzyl-2-(N-benzyloxyamino)-2-methylbutane-1,3,4-triol 
• 211045-04-4 (2R,3R)-3,4-di-O-benzyl-2-(N-benzyloxyamino)-2-phenylbutane-1,3,4-triol 
• 188909-35-5 O-Benzyl-N-[(R)-1-((R)-1,2-bis-benzyloxy-ethyl)-1-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-hydroxylamine 

Relevant academic research and scientific papers

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.

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.