40597-41-9

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 69277-00-5 N¹-Methyl-N²,N²-dimethylformohydrazid-4-methylphenylsulfonylimid 
• 76291-40-2 N-[1-(N'-Isopropylidene-hydrazino)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide 
• 76291-42-4 N-[1-[N'-(1-Isopropyl-2-methyl-propylidene)-hydrazino]-meth-(E)-ylidene]-4-methyl-benzenesulfonamide 
• 76291-46-8 N-[1-(N'-Benzhydrylidene-hydrazino)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide 
• 76291-45-7 4-Methyl-N-[1-{N-methyl-N'-[1-phenyl-eth-(Z)-ylidene]-hydrazino}-meth-(E)-ylidene]-benzenesulfonamide 
• 131544-26-8 2,4-dimethyl-3-(N-tosylamino)-1,4-pentadiene 
• 1312037-39-0 6-(3,5-dimethylphenyl)-3-(p-toluenesulfonyl)-2-vinyl-3-azabicyclo[4.1.0]hept-4-ene 
• 1312037-40-3 6-(4-methoxyphenyl)-3-(p-toluenesulfonyl)-2-vinyl-3-azabicyclo[4.1.0]hept-4-ene 
• 1312037-41-4 6-(3-methoxyphenyl)-3-(p-toluenesulfonyl)-2-vinyl-3-azabicyclo[4.1.0]hept-4-ene 
• 1312037-31-2 N-(3-(3, 5-dimethylphenyl)prop-2-yn-1-yl)-4-methyl-N-(penta-1,4-dien-3-yl)benzenesulfonamide 
• 1312037-32-3 N-(3-(4-methoxyphenyl)prop-2-yn-1-yl)-4-methyl-N-(penta-1,4-dien-3-yl)benzenesulfonamide 
• 1312037-33-4 N-(3-(3-methoxyphenyl)prop-2-yn-1-yl)-4-methyl-N-(penta-1,4-dien-3-yl)benzenesulfonamide 
• 1312037-34-5 4-methyl-N-(3-(4-nitrophenyl)prop-2-ynyl)-N-(penta-1,4-dien-3-yl)benzenesulfonamide 
• 1312037-35-6 C₁₂H₁₅NO₂S 

Relevant academic research and scientific papers

Enantioselective Rh(II)-Catalyzed Desymmetric Cycloisomerization of Diynes: Constructing Furan-Fused Dihydropiperidines with an Alkyne-Substituted Aza-Quaternary Stereocenter

Described herein is an enantioselective dirhodium(II)-catalyzed cycloisomerization of diynes achieved by the strategy of desymmetrization, which not only represents a new cycloisomerization reaction of diynes but also constitutes the first Rh(II)-catalyzed asymmetric intramolecular cycloisomerization of 1,6-diynes. This protocol provides a range of valuable furan-fused dihydropiperidine derivatives with an enantiomerically enriched alkynyl-substituted aza-quaternary stereocenter in high efficiency, complete atom economy, and excellent enantioselectivity (up to 98% ee). Besides, the highly functionalized products could be easily transformed into various synthetically useful building blocks and conjugated with a series of pharmaceutical molecules. The mechanism involving a concerted [3+2] cycloaddition/[1,2]-H shift of the Rh(II) carbenoid intermediate was elucidated by DFT calculations and mechanistic studies. More importantly, the first single crystal of alkyne-dirhodium(II) was obtained to show that a η2-coordinating activation of alkynal by dirhodium(II) was involved. Weak hydrogen bondings between the carboxylate ligands and alkynal were found, which probably made the well-defined paddlewheel-like dirhodium(II) distinctive from other metal complexes in catalyzing this transformation. Furthermore, the origin of the enantioselectivity was elucidated by a Rh2(R-PTAD)4-alkyne complex and additional calculational studies.