1306740-68-0

Upstream product

• 100-52-7 benzaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 1208066-51-6 (R_S,S)-N-(1-(phenyl)but-3-yn-1-yl)-2-methylpropane-2-sulfinamide 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 24395-14-0 (R)-2-phenyl-N-tosylaziridine 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 1179523-29-5 (S)-2-phenyl-1-tosylpyrrolidine 
• 1567395-39-4 (S)-5-phenyl-1-tosylpyrrolidin-3-one 
• 938-36-3 (S)-(-)-1-methyl-2-phenylpyrrolidine 
• 56553-09-4 (S)-(-)-5-phenylpyrrolidin-2-one 
• 1426257-00-2 (S)-5-phenyl-1-tosylpyrrolidin-2-one 
• 1361969-83-6 4-methyl-N-((R)-1-(pentyloxy)allyl)-N-((S)-1-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 1361969-76-7 4-methyl-N-[(1S)-1-(pentyloxy)prop-2-en-1-yl]-N-[(1S)-1-phenylbut-3-yn-1-yl]benzene-1-sulfonamide 
• 1361970-15-1 (2S,6R)-2-phenyl-1-tosyl-6-vinylpiperidin-4-one 
• 1361970-10-6 (2S,6S)-2-phenyl-1-tosyl-6-vinylpiperidin-4-one 
• 1361970-02-6 (2S,6S)-4-(pentyloxy)-2-phenyl-1-tosyl-6-vinyl-1,2,3,6-tetrahydropyridine 
• 1361969-97-2 (2S,6R)-4-(pentyloxy)-2-phenyl-1-tosyl-6-vinyl-1,2,3,6-tetrahydropyridine 

Relevant academic research and scientific papers

Stereospecific Synthesis of cis-2,5-Disubstituted Pyrrolidines via N, O-Acetals Formed by Hydroamination Cyclization-Hydroalkoxylation of Homopropargylic Sulfonamides in HFIP

We reported a novel two-step stereoselective synthesis of functionalized pyrrolidines from homopropargylic sulfonamides and nucleophiles via an isolable N,O-acetal intermediates. This reaction features mild conditions and good scope of substrates. In addition, the use of hexafluoroisopropanol, acting as a solvent, an additive, a weak nucleophile, and a good leaving group, is pivotal to the success of the method. Moreover, reactions of chiral homopropargylic sulfonamides afford only 2,5-cis-disubstituted pyrrolidines with high diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to >99% ee). The overall reaction constitutes a formal 1,1-bifunctionalization of terminal alkynes, which has hitherto been reported only rarely. Additionally, this method provides efficient access to pharmaceutical intermediate and to carry out postmodification of natural products.

Stereoselective synthesis of 2,5-disubstituted pyrrolidines: Via gold-catalysed anti-Markovnikov hydroamination-initiated tandem reactions

A series of gold-catalysed intramolecular anti-Markovnikov hydroamination-initiated azidation, allylation and heteroarylation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 2,5-disubstituted pyrrolidines are obtained in moderate to excellent yields with excellent enantioselectivities and generally high diastereoselectivities.

Gold-Catalyzed Tandem Cycloisomerization-Halogenation of Chiral Homopropargyl Sulfonamides

Two new gold-catalyzed tandem cycloisomerization-halogenation reactions of chiral homopropargyl sulfonamides have been developed. Various enantioenriched 3,3-diiodopyrrolidin-2-ols and 3-fluoropyrrolidin-2-ols were obtained in moderate-to-good yields with excellent enantio- and diastereoselectivity.

Efficient and practical synthesis of enantioenriched 2,3-dihydropyrroles through gold-catalyzed anti-Markovnikov hydroamination of chiral homopropargyl sulfonamides

A direct gold-catalyzed 5-endo-dig cycloisomerization of chiral homopropargyl sulfonamides has been developed. A range of enantioenriched 2,3-dihydropyrroles are readily accessed by utilizing this approach. Importantly, this gold-catalyzed cycloisomerization reaction proceeds through an anti-Markovnikov addition by using a catalytic base as the additive, which completely suppresses the undesired dimerization. This journal is

Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: A reliable access to enantioenriched pyrrolidin-3-ones

A gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides has been developed, which provides a reliable access to synthetically useful chiral pyrrolidin-3-ones with excellent ee, by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. This methodology has also been used in the facile synthesis of natural product (-)-irniine. The use of readily available starting materials, a broad substrate scope, a simple procedure and the mild nature of this reaction render it a viable alternative for the synthesis of enantioenriched pyrrolidin-3-ones.

Gold-catalyzed oxidative cyclization of chiral homopropargyl amides: Synthesis of enantioenriched γ-lactams

A gold-catalyzed tandem cycloisomerization/oxidation of homopropargyl amides has been developed, which provides ready access to synthetically useful chiral γ-lactams with excellent ee by combining the chiral tert-butylsulfinimine chemistry and gold cataly

Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines

We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.