181303-69-5

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 622-30-0 N-benzyl hydroxylalmine 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 1066-54-2 trimethylsilylacetylene 
• 54655-07-1 lithium trimethylsilylacetylenide 

Downstream Products

• 181303-63-9 (R)-N-benzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-amine 
• 198418-05-2 methyl (2S,3S)-2-(acetoxyamino)-N-benzyl-3,4-dihydroxy-3,4-O-isopropylidenebutanoate 
• 198418-04-1 (3R,4S)-3-(acetoxyamino)-N-benzyl-4,5-dihydroxy-4,5-O-isopropylidene-1-pentyne 
• 198418-03-0 N-Benzyl-N-[(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-prop-2-ynyl]-hydroxylamine 

Relevant academic research and scientific papers

Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, 3- O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and βhydroxy-α-amino acids

The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene- D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N. hydroxy α-amino esters 8 and 13 as well as the corresponding α-amino esters 9 and 14.

Direct vinylation and ethynylation of nitrones. Stereodivergent synthesis of allyl and propargyl amines

The addition of vinyl and ethynyl organometallic reagents to the nitrone derived from D-glyceraldehyde affords allyl and propargyl hydroxylamines which are easily converted into the corresponding allyl and propargyl amines. The stereoselectivity of the addition step can be controlled by the presence (or absence) of diethyl aluminium chloride.