168984-99-4

Upstream product

• 97401-93-9 N-(p-toluenesulfonyl)-2-(4-chlorophenyl)aziridine 
• 762-72-1 allyl-trimethyl-silane 
• 98-59-9 p-toluenesulfonyl chloride 
• 140-53-4 p-chlorobenzyl cyanide 
• 7393-43-3 tetraallyl tin 
• 1730-25-2 allylmagnesium bromide 

Relevant academic research and scientific papers

Scandium triflate-catalyzed 1,3-dipolar cycloaddition of aziridines with alkenes

Phenyl aziridines undergo 1,3-dipolar cycloaddition efficiently with olefins such as cyclic enol ethers and allyltrimethylsilane in the presence of a catalytic amount of Sc(OTf)3 at ambient temperature to afford the corresponding pyrrolidine derivatives in high yields with high regioselectivity.

Ring opening of phenylaziridines with allylsilanes

N-tosyl phenylaziridines are opened regioselectively with allylsilanes in presence of BF3.ET2O to form γ-amino olefins. During the reaction a formal [3+2] cycloaddition produced the corresponding pyrrolidines, amenable to the open chain compounds with TBAF.

Bi(OTf)3-catalyzed allylation of epoxides: A facile synthesis of homoallylic alcohols

Epoxides react smoothly with tetraallyltin in the presence of 2 mol% of Bi(OTf)3 under mild reaction conditions to afford the corresponding homoallylic alcohols in excellent yields with high regioselectivity while aryl aziridines produce exclusively allyl amines in good yields under similar conditions.

An efficient synthesis of (±)-4-amino-3-(4-chlorophenyl)-butyric acid. (baclofen)

A new preparation of baclofen is proposed. The key step involved a regioselective ring opening of 2-phenylaziridine with allylmagnesium bromide. Further oxidation of the side chain gives access to 4-phenyl-pyrrolidin-2-one and to baclofen.

Palladium-catalyzed highly selective intramolecular bromoamination of alkenes: Efficient synthesis of substituted pyrrolidines

A new method has been developed for the preparation of substituted pyrrolidines by the palladium-catalyzed intramolecular bromoamination of substituted aminoalkenes. The catalytic system and reaction conditions used for this transformation have been fully optimized. Notably, this reaction exhibits excellent selectivity, affording the pyrrolidine products as single 5-exo-bromoalkylpyrrolidines in excellent yields. Furthermore, this reaction occurs at room temperature under mild conditions, reaching completion within 1?h.

Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes

A photoredox catalyzed aminodifluoromethylation of unactivated alkenes has been developed in which HCF2SO2Cl is used as the HCF2 radical source. Sulfonamides were active nucleophiles in the final step of a tandem addition/oxidation/cyclization process to form pyrrolidines, and esters were found to cyclize to form lactones. Thus, a variety of pyrrolidines and lactones were obtained in moderate to excellent yield. In order for the cyclization reactions to be efficient, a combination of a copper catalyst (Cu(dap)2Cl) and silver carbonate was crucial to suppressing a competing chloro, difluoroalkylation process.