96013-56-8

Upstream product

• 917-64-6 methyl magnesium iodide 
• 96013-55-7 1-[(4-methylphenyl)sulfonyl]-5,6-dihydro-1H-piperidin-2-one 
• 626-58-4 4-methylpiperidin 
• 75-16-1 methylmagnesium bromide 
• 60212-39-7 4-methyl-1-tosylpiperidine 
• 104375-65-7 4-methyl-N-(3-methylpent-4-en-1-yl)benzenesulfonamide 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 51174-44-8 3-methyl-4-penten-1-ol 
• 1257867-21-2 3-methyl-N-tosylpyrrolidine-2-carbaldehyde 
• 1257867-34-7 (3-methyl-N-tosylpyrrolidin-2-yl)methanol 
• 23438-61-1 1-(toluene-4-sulfonyl)piperidin-2-one 
• 675-20-7 piperidin-2-one 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 646996-64-7 1-[4-methyl-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]cyclobutanol 
• 317339-77-8 4-methyl-1-tosyl-5,6-dihydropyridin-2(1H)-one 
• 626232-96-0 6-(1-ethoxybuta-1,3-dienyl)-4-methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 
• 626232-87-9 trifluoromethanesulfonic acid 4-methyl-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl ester 

Relevant academic research and scientific papers

Platinum-Catalyzed Desaturation of Lactams, Ketones, and Lactones

The development of a general platinum-catalyzed desaturation of N-protected lactams, ketones, and lactones to their conjugated α,β-unsaturated counterparts is reported. The reaction operates under mildly acidic conditions at room temperature or 50 °C. It is scalable and tolerates a wide range of functional groups. The complementary reactivity to the palladium-catalyzed desaturation is demonstrated in the efficient conversion of iodide, bromide, and sulfur-containing substrates.

NHC-Catalyzed intramolecular redox amidation for the synthesis of functionalized lactams

A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.

Synthesis of functionalized 1-azaspirocyclic cyclopentanones using bronsted acid or N-bromosuccinimide promoted ring expansions

Azaspirocyclic ring systems are present in a variety of alkaloids. Functionalized 1-azaspirocyclopentanones (6, 7, 11, 12) can be efficiently constructed through semipinacol ring expansion reactions of 2-(1- hydroxycyclobutyl)-p-toluenesulfonylenamides (4

New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction

The Pd-catalyzed coupling reaction of lactam or lactone-derived vinyl triflates and phosphates with α-alkoxydienylboronates gives conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety. If subjected to mild acidic hydrolysis, these compounds undergo a 4π electrocyclization process (Nazarov reaction) which furnishes cyclopenta-fused O- and N-heterocycles in good yields. The scope of the work has been that of closely examining the role and effect of both the heteroatom and the heterocycle ring size on the outcome of the electrocyclization, as well as the torquoselectivity of this process. The presence of the heteroatom was essential in stabilizing the oxyallyl cation intermediate, thus allowing the reaction to occur. The ring size was also a basic parameter in the cyclization step: five-membered azacycles required more drastic conditions to give 5-5 fused systems and did so only after an initial hydrolysis to the corresponding divinyl ketones. As for the torquoselectivity, with both 2-methyl and 4-methyl substituted lactam derivatives steric interactions seem to have a role in forcing the conrotatory process to take place in one sense only: allowing the synthesis of diastereomerically pure compounds to be realized. Because different patterns of substitution on the heterocycle are compatible with the reaction conditions, the methodology developed could be very useful for the synthesis of natural products and biologically active compounds containing cyclopenta-fused O- and N-heterocycle moieties.

CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO N-TOSYLATED α, β-UNSATURATED AMIDES

N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.).Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure.The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.