137945-72-3

Upstream product

• 109-87-5 Dimethoxymethane 
• 90365-74-5 (3S,4S)-(+)-1-benzyl-3,4-pyrrolidinediol 
• 75172-31-5 (3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dione 
• 100-46-9 benzylamine 
• 100449-52-3 (+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate 
• 99891-36-8 (-)-(2S,3S)-2,3-bis(methoxymethoxy)butane-1,4-diol 
• 212902-08-4 (2S,3S)-2,3-bis(methoxymethyloxy)-4-(methylsulfonyloxy)butyl methanesulfonate 

Downstream Products

• 159180-58-2 (2S,3S,4S)-2-(4-Methoxy-benzyl)-3,4-bis-methoxymethoxy-pyrrolidine 
• 159180-55-9 (2-Amino-phenyl)-((3S,4S)-3,4-bis-methoxymethoxy-pyrrolidin-1-yl)-methanone 
• 100449-58-9 (2R,3S,4S)-2-(4-methoxybenzyl)-3,4-O-bis-(methoxymethyl)pyrrolidine 

Relevant academic research and scientific papers

Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

Cycloadditions of 3,4-isopropylidenedioxy-Δ1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-Δ1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.

Synthesis of nitrones using the methyltrioxorhenium/hydrogen peroxide system

Secondary amines are oxidized by the methyltrioxorhenium/hydrogen peroxide system to the corresponding nitrones in excellent yield. The results provide a further example of the parallel between the chemistry of this metal system and that of the dioxiranes.