462996-06-1

Upstream product

• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 107-18-6 allyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 106-95-6 allyl bromide 

Downstream Products

• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 1190988-00-1 tert-butyl 2-oxoethyl(tosyl)carbamate 
• 594858-64-7 N-allyl-4-methyl-N-(2-methylallyl)benzenesulfonamide 
• 952688-49-2 N-allyl-N-((2E)-2-butenyl)-p-toluenesulfonamide 
• 483370-09-8 N-allyl-N-but-3-enyl-4-methyl-benzenesulfonamide 
• 386750-63-6 N-allyl-N-(4-hydroxybut-2-yn-1-yl)-4-methylbenzenesulfonamide 
• 1346228-67-8 C₂₁H₂₁NO₄S 

Relevant academic research and scientific papers

Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles

Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.

Au-catalyzed piperidine synthesis via tandem acyloxy migration/ intramolecular [3 + 2] cycloaddition of enynyl esters

An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of

An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols

Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargyllc alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles In minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.

Cycloisomerization promoted by the combination of a ruthenium-carbene catalyst and trimethylsilyl vinyl ether, and its application in the synthesis of heterocyclic compounds: 3-Methylene-2,3-dihydroindoles and 3-methylene-2,3- dihydrobenzofurans

Substituted N and O heterocycles have been synthesized by the cycloisomerization of dienes using a ruthenium-carbene catalyst. The products obtained with and without trimethylsilyl vinyl ether differ (see scheme, Cy = cyclohexyl, Mes = 2,4,6-trimethylphenyl, Ts = p-toluenesulfonyl).

Fluorous Mitsunobu reagents and reactions

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse.