157367-96-9

Upstream product

• 349098-69-7 N-(4-methylpentyl)-4-methylbenzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 25163-50-2 4-methyl-4-pentenyl-1-tosylate 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 22508-64-1 4-methyl-4-penten-1-ol 
• 691900-28-4 N-(tert-butoxycarbonyl)-N-(4-methylpent-4-enyl)-4-methylbenzenesulfonamide 
• 73541-16-9 5-iodo-2-methylpent-1-en 

Downstream Products

• 691900-13-7 N-ethynyl-4-methyl-N-(4-methyl-pent-4-enyl)-benzenesulfonamide 
• 691900-36-4 N-(2,2-dichlorovinyl)-N-(4-methylpent-4-enyl)-4-methylbenzenesulfonamide 
• 1322093-54-8 2-(bromomethyl)-2-methyl-1-tosylpyrrolidine 
• 1403817-97-9 (+/-)-(2-methyl-1-tosylpyrrolidin-2-yl)methanol 
• 691900-33-1 N-formyl-N-(4-methylpent-4-enyl)-4-methylbenzenesulfonamide 

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

A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization

Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.

Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes

The RhII-catalyzed oxyamination and diamination of alkenes generate 1,2-amino alcohols and 1,2-diamines, respectively, in good to excellent yields and with complete regiocontrol. In the case of diamination, the intramolecular reaction provides

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.

Radical cascade cyclizations and platinum(II)-catalyzed cycloisomerizations of ynamides

Ynamides are tested as new partners in radical and organometallic transformations. A radical cascade involving a 5-exo-dig cyclization followed by a 6-endo-trig radical trapping transforms ynamides into hetero-polycyclic compounds such as isoindoles, isoindolinones and pyrido-isoindolones. Various ene-tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This unprecedented and easily operated process can be coupled with a hydrolysis of the intermediate cyclic tosylenamides in a one-pot transformation, which provides cyclobutanones.

Platinum dichloride-catalyzed cycloisomerization of ene-ynamides

Various ene-tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This unprecedented and easily operated process can be coupled with a hydrolysis of the intermediate cyclic tosylenamides in a one-pot transformation

Synthesis of pyrrolidines and piperidines via palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides

The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.