167613-40-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1099592-54-7 C₁₇H₂₉N₃O₃Si 
• 929722-00-9 C₁₇H₂₉N₃O₃Si 
• 78469-85-9 (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol 
• 123833-71-6 (2S,3S)-4-benzyloxy-1-tert-butyldimethylsiloxy-2,3-epoxybutane 

Downstream Products

• 115344-31-5 (2S,3S)-3-(benzyloxy)methyl-1-(4-methylphenyl)sulfonyl-2-aziridinemethanol 
• 167029-59-6 N-((R)-2-Benzyloxy-1-(R)-oxiranyl-ethyl)-4-methyl-benzenesulfonamide 
• 929722-04-3 2-benzyloxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol 

Relevant academic research and scientific papers

Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.

Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.

Synthesis of optically pure 2-Aziridinemethanols: Versatile synthetic building blocks

Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2,3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-a