107301-61-1

Upstream product

• 36832-51-6 1-(but-3-yn-1-ylsulfonyl)-4-methylbenzene 
• 100-46-9 benzylamine 
• 192989-95-0 1-methanesulfonyl-3-butyn 
• 72486-09-0 methanesulfonic acid but-3-ynyl ester 
• 227030-66-2 (+/-)-1-benzylazetidine-2-carbonitrile 
• 927-74-2 3-Butyn-1-ol 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 

Downstream Products

• 143427-63-8 1-Benzyl-4-iodo-1,2,5,6-tetrahydropyridine 
• 107301-64-4 N-benzyl-N-(4-butynyl)trifluoromethanesulfonamide 
• 142301-75-5 N-(tert-butoxycarbonyl)-N-benzyl-4-amino-1-butyne 
• 143427-64-9 N-benzylpenta-3,4-dien-2-amine 
• 143427-62-7 1-Benzyl-4-bromo-6-methyl-1,2,3,6-tetrahydro-pyridine 
• 143427-60-5 1-Benzyl-4-iodo-6-methyl-1,2,3,6-tetrahydro-pyridine 
• 107301-95-1 6-Benzylamino-hex-3-yn-2-ol 
• 107301-65-5 ethyl N-benzyl-N-(4-butynyl)oxamate 
• 142301-77-7 Ethyl 5-(benzylamino)pent-2-ynoate 
• 142301-78-8 Ethyl 5-pent-2-ynoate 
• 142301-79-9 Ethyl (Z)-5-pent-2-enoate 
• 112548-81-9 (3-Acetyl-1-benzyl-piperidin-4-yl)-acetic acid ethyl ester 
• 1067676-15-6 dimethyl 2-(N-benzyl-N-(but-3-ynyl)amino)malonate 
• 38025-34-2 4-ethyl-1,2,3,6-tetrahydro-1-(phenylmethyl)-pyridine 

Relevant academic research and scientific papers

Synthesis of homopropargylamines from 2-cyanoazetidines

2-Cyanoazetidines, easily accessible from β-amino alcohols, undergo ring-cleavage upon reaction with trimethylsilylazide and catalytic amounts of Bu2SnO, to give the corresponding homopropargylamines which are isolated as their N-Boc protected

Biogenetically inspired total syntheses of lycopodium alkaloids, (+)-flabellidine and (-)-lycodine

The first asymmetric total synthesis of (+)-flabellidine (2) and the shortest total synthesis of (-)-lycodine (3) were accomplished by a strategy featuring the one-pot construction of a tetracyclic lycodine skeleton from a linear precursor, which was insp

Iodocarbamation of N-Homopropargyl Carbamates: Mild and Stereoselective Entry to Functionalized Oxazinan-2-ones

An efficient and general iodocarbamation of benzyl N-homopropargylcarbamates has been developed by using iodine as the electrophilic agent. This regio- and stereoselective cyclization yielded (E)-6-iodomethyleneoxazinan-2-ones, which can be further transformed through palladium cross-coupling reactions followed by hydrogenation to produce 1,3-oxazinan-2-ones.

Rhodium-Catalyzed Intramolecular C-H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds

On treatment of triazoles having an N-sulfonyl-protected benzylamine moiety with [Rh2(C7H15CO2)4], intramolecular C-H bond insertion takes place at the benzylic position to give cis-N-sulfonyl-2-aryl-3-[(sulfonylimino)methyl]pyrrolidines in good yields and with highly stereoselectivities. Analogously, the similar treatment of triazoles having an ether or even an alkyl moiety affords 2-alkyl- or 2-aryl-3-[(sulfonylimino)methyl]tetrahydrofurans or a 2-alkyl-3-[(sulfonylimino)methyl]cyclopentane in good yields. Three is a magic number: On treatment of triazoles with [Rh2(C7H15CO2)4], the rhodium catalyst plays three roles, denitrogenation, C-H bond activation, and stereoselective cyclization, providing a new method for heterocycle synthesis. Intramolecular C-H bond insertion takes place at the benzylic position to give pyrrolidines and related heterocycles in good yields.

Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis

The combination of triazole/gold (TA-Au) and Cu(OTf)2is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C?B bond formation.

Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades

The enantioselective synthesis of heavily decorated spirolactams has been accomplished via an arylative or vinylative allene carbocyclisation cascade. Mediated by silver phosphate, a range of allene-linked pro-nucleophiles and aryl or vinyl iodides were reacted in the presence of catalytic Pd(OAc)2 and chiral bis(oxazoline) ligands to afford the spirolactam products in good yields and high enantio- and diastereoselectivities. The Royal Society of Chemistry 2013.

Synthesis of α-CN and α-CF3 N-heterocycles through tandem nucleophilic additions

Using a readily available secondary aminoalkyne as starting material, a powerful strategy was discovered to prepare precursors of biologically important unnatural cyclic aminoacids and fluorinated N-heterocycles with important ring sizes (e.g., 5-7) in a

Palladium-catalysed cyclisation of N-alkynyl aminomalonates

Go around in (hetero)cycles! The palladium-catalysed tandem cyclisation/coupling reaction of alkynyl- and alkenyl-substituted aminomalonates leads to highly functionalised pyrrolidines and piperidines in good yield (see scheme). The reaction allows efficient access to a broad range of synthetically valuable building blocks.

Gold-catalyzed synthesis of alkylidene 2-oxazolidinones and 1,3-oxazin-2-ones

N-Boc-protected alkynylamines are converted into the corresponding alkylidene 2-oxazolidinones or 2-oxazinones under very mild reaction conditions in the presence of 1-5 mol % of a cationic Au(I) complex. The scope of the reaction is very general, providi

Carbene reactions of α-oxacyclo- and α-azacyclo-N-aziridinylimines: Effect of heteroatom and ring size in the ring expansion reaction

Carbenes, generated from thermolysis of α-oxacyclo- and α-azacyclo-N-aziridinylimines in refluxing toluene, underwent ring expansions via insertion of alkyl carbenes into carbon-carbon bonds and intramolecular ammonium ylide formations, respectively. Ring expansion reaction of α-oxetanyl-N-aziridinylimines occurred via alkylidenecarbene intermediates, whereas thermal reaction of α-azetidinyl-N-aziridinylimines afforded α-aminoacetylene compounds via 1,2-H migration of alkylidenecarbene intermediates.