211188-18-0

Upstream product

• 622-33-3 N-benzyloxyamine 
• 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 
• 188909-29-7 O-Benzyl-N-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-ethyl]-hydroxylamine 
• 211044-91-6 (2R,3R)-3,4-O-isopropylidene-2-(N-benzyloxyamino)-2-methylbutane-1,3,4-triol 
• 188909-47-9 (4R)-3-benzyloxy-4-methyl-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-oxazolidin-2-one 

Downstream Products

• 188909-51-5 (2R)-3-hydroxy-2-(N-benzyloxyamino)-2-methylpropionic acid 
• 188909-49-1 (4R)-3-benzyloxy-4-methyl-4-methoxycarbonyl-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Stereoselective synthesis of α-substituted serines from protected erythrulose oximes

The additions of organolithium reagents to the C=N bond of several chiral oxime ethers derived from erythrulose afforded protected amino polyols with high diastereoselectivity. Four of the latter compounds have been convened into the α,α-disubstituted α-amino acids (R)-2-(-)-methylserine, (S)-2-(+)-methylserine, (R)-(+)-2-phenylserine and (R)-(-)-2-n-butylserine.

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.