210347-80-1

Upstream product

• 100-39-0 benzyl bromide 
• 148759-65-3 (S)-(-)-1-Allyl-2-hydroxymethylpyrrolidin 
• 152668-35-4 Methyl 1-(2-propenyl)pyrrolidine-2-carboxylate 
• 89597-97-7 (2S)-benzyloxymethyl-pyrrolidine 
• 106-95-6 allyl bromide 

Downstream Products

• 1026152-96-4 [(R)-1-((S)-2-Benzyloxymethyl-pyrrolidine-1-carbonyl)-but-3-enyl]-(2,2-diethoxy-ethyl)-carbamic acid tert-butyl ester 
• 1026390-17-9 (R)-1-((S)-2-Benzyloxymethyl-pyrrolidin-1-yl)-2-[(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-(2,2-diethoxy-ethyl)-amino]-pent-4-en-1-one 
• 1291079-41-8 (S,E)-2-benzyloxymethyl-1-(2'-tosylpent-1',4'-dien-1'-yl)pyrrolidine 

Relevant academic research and scientific papers

Asymmetric α-2-tosylvinylation of in situ-generated N-2-tosylvinyl proline-derived ammonium ylides

Asymmetric α-2-tosylvinylation of N-substituted proline esters using ethynyl tolyl sulfone as an electrophile was shown to proceed in good yield with high enantioselectivities without the addition of any bases. The reaction proceeds via the formation of N-2-tosylvinyl ammonium ylides.

Synthesis of optically active C-allylglycine derivatives and conversion into isoquinolones

C-Allylglycyl amides can be efficiently synthesized via an auxiliary controlled diastereoselective aza-Claisen rearrangement. The stereodirecting unit is placed on an auxiliary derived from commercially available (S)-proline. After N-allylation, the obtained optically active allylamines were reacted with various N-protected glycyl fluorides to give the (2R)-C-allylglycyl amides in good yields. The diastereoselectivity of the asymmetric allylation varied between 1:1 and > 1:15 depending on the N-protective group, the auxiliary, and the reaction temperature. Likewise, the C-allylglycine derivatives can be used as monomers in peptide synthesis to synthesize (R)-proline derivatives or chiral isoquinolones; the latter should serve as building blocks in the total syntheses of alkaloids.