16079-17-7

Upstream product

• 2978-58-7 1,1-dimethylprop-3-ynylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1010698-14-2 C₁₃H₁₉NO₃S 

Downstream Products

• 139372-13-7 (Z)-4,4-dimethyl-3-[(dimethyl-phenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one 
• 121239-42-7 N-(1,1-dimethyl-2-oxopropyl)-p-toluenesulfonamide 
• 875612-05-8 (Z)-3-methyl-2-[(dimethyl-phenylsilyl)methylene]-3-(p-tosylamino)butanal 
• 144776-79-4 2-(dimethylphenylsilylmethyl)-3-methyl-2-butenal 
• 875612-12-7 (Z)-3-methyl-2-[(dimethyl-4-methoxyphenylsilyl)methylene]-3-(p-tosylamino)butanal 
• 139372-13-7 C₂₁H₂₅NO₃SSi 

Relevant academic research and scientific papers

Rhodium-Catalyzed [5+2] Cycloaddition of 3-Acyloxy-1,4-enyne with Alkene or Allene

We recently developed a completely new type of Rh-catalyzed [5+2] cycloaddition by using 3-acyloxy-1,4-enyne (ACE) as the 5-carbon building block. In this update, we show that ACE can undergo intramolecular [5+2] cycloaddition with either an alkene or an allene in the presence of an appropriate rhodium catalyst and ligands to afford bicyclic compounds with multiple stereogenic centers. In most cases, cis-fused bicyclo[5.3.0]decadienes are prepared highly diastereoselectively. (Figure presented.) .

Ambient Synthesis of Tricyclic Naphthalenes via Stepwise Styryl-yne Dearomative Diels-Alder Cyclization

A cascade of styrylynols promoted by MnO2 allows the synthesis of fused tricycles with a naphthalene core. The reaction occurs under ambient conditions, offering a practical synthetic tool because of the inexpensive and abundant manganese species. The met

Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds

We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl2/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of functional groups and provides high value intermediates with two distinct functional handles. The synthetic applicability of the reaction has been shown through the synthesis of diverse ambiphilic aziridines.

Fluorocyclization of Allyl Alcohols and Amines to Access 3-Functionalized Oxetanes and Azetidines

An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N3 or -OR) plays a crucial role in polarizing the C= C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.

Mechanistic Insights into the Ru(II)-Catalyzed Intramolecular Formal [3 + 2] Cycloaddition of (E)-1,6-Enynes

Design of a unique reaction pathway in transition-metal-catalyzed 1,6-enynes cyclization to construct valuable synthetic motifs is a significant challenge in organic chemistry. Herein, we report a Ru(II)-catalyzed formal [3 + 2] cycloaddition as an efficient method to prepare unprecedented bicyclo[3.3.0]octenes from readily available (E)-1,6-enynes. Mechanistic studies based on the deuterium labeling experiments and the DFT calculation disclose a reasonable mechanistic pathway, where a ruthenacyclopentene generated by an ene-yne oxidative cyclization undergoes a sequential ?-hydride elimination and intramolecular hydroruthenation to form a ruthenacyclohexene, producing the desirable bicyclo[3.3.0]octenes.

A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis

This work reports the construction of cyclopentene cores from 1,6-enynes and aryl diazo ketones through two new reaction sequences involving initial gold-catalyzed cyclization of 1,6-enynes with diazo species, followed by rhodium-catalyzed skeletal rearrangement of the resulting 3-cyclopropyl-2-en-1-ones. In most instances the rhodium-catalyzed reactions afforded cyclopentene derivatives whereas several n-alkyl- or ortho-substituted phenyl ketones delivered seven-membered oxacycles. A plausible mechanism provides rationales for these two distinct products. (Figure presented.).

Facile synthesis, characterization, and antimicrobial studies of some disubstituted 1,2,3-triazoles with sulfonamide functionality

An expedient synthesis of some 1,4-disubstituted 1,2,3-triazoles (3a–3x) having sulfonamide functionality from various terminal alkynes and aromatic azides through Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition has been reported. The structures of newl

Ruthenium-Catalyzed Hydroalkynylative Cyclization of 1,6-Enynes Induced by Substituent Effects

The ruthenium-catalyzed 1,6-enyne cyclization in the presence of bulky substituted terminal alkyne proceeds smoothly at room temperature to afford highly substituted five-membered cyclic compounds featuring a 1,5-enyne motif. Deuterium-labeling experiment

Rhodium-catalyzed carbonylative [3 + 2 + 1] cycloaddition of alkyne-tethered alkylidenecyclopropanes to phenols in the presence of carbon monoxide

A novel Rh-catalyzed carbonylative [3 + 2 + 1] cycloaddition of alkyne-tethered alkylidenecyclopropanes for the facile synthesis of bicyclic phenols in high yields has been developed. The reaction tolerated carbon and heteroatoms in the tether.

Cyclobutene formation in PtCl2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes

Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl 2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes featuring a terminal alkyne and amide as the solvent. It is shown that the weak coordinating properties of the solven