419554-93-1

Upstream product

• 55108-01-5 1-aminohex-trans-4-ene 
• 98-59-9 p-toluenesulfonyl chloride 
• 99097-68-4 (E)-2-(hex-4-en-1-yl)isoindoline-1,3-dione 
• 112683-29-1 (E)-1-iodo-4-hexene 
• 70-55-3 toluene-4-sulfonamide 
• 1143-01-7 N-hexyl p-toluenesulfonamide 
• 145472-39-5 1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinol 
• 928-92-7 (E)-hex-4-en-1-ol 
• 60653-76-1 <(E)-4-Hexenyl>-methansulfonat 

Downstream Products

• 116699-99-1 1-tosyl-2-vinyl-pyrrolidine 
• 124920-12-3 2-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine 
• 54356-23-9 (S)-2-ethyl-1-tosylpyrrolidine 
• 905982-99-2 (R)-2-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 

Relevant academic research and scientific papers

Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines

A majority of medicines contain a nitrogen atom within a five- or six-membered ring. To rapidly access both such aza-heterocycles, we sought to develop a remote C–H desaturation of amines. Inspired by the Hofmann-L?ffler-Freytag (HLF) synthesis of five-me

Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.

Synthetic efforts toward the Lycopodium alkaloids inspires a hydrogen iodide mediated method for the hydroamination and hydroetherification of olefins

Progress toward the total syntheses of a diverse set of fawcettimine-type Lycopodium alkaloids via a "Heathcock-type" 6-5-9 tricycle is disclosed. This route features an intermolecular Diels-Alder cycloaddition to rapidly furnish the 6-5-fused bicycle and a highly chemoselective directed hydrogenation to build the azonane fragment. While conducting these synthetic studies, trimethylsilyl iodide was found to effect a hydroamination reaction to furnish the tetracyclic core of serratine and related natural products. This observation has been expanded into a general method for the room temperature hydroamination of unactivated olefins with tosylamides utilizing catalytic "anhydrous" HI (generated in situ from trimethylsilyl iodide and water). The presence of the iodide anion is critical to the success of this Bronsted acid catalyzed protocol, possibly due to its function as a weakly coordinating anion. These conditions also effect the analogous hydroetherification reaction of alcohols with unactivated olefins.

Electrophilic cyclization of N-alkenylamides using?a chloramine-T/I2 system

A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I2 system functions as an effective iodonium species.