54838-69-6

Upstream product

• 201230-82-2 carbon monoxide 
• 1160516-53-9 4-[3-(1-phenyl-allyloxy)-prop-1-ynyl]-benzene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 2687-12-9 cinnamyl chloride 

Downstream Products

• 1203539-49-4 (1S,6S,7R)-6,7-diphenyl-3-oxabicyclo[4.1.0]hept-4-ene 
• 1398654-89-1 (1R,6R,7S)-6,7-diphenyl-3-oxabicyclo[4.1.0]hept-4-ene 
• 79801-99-3 1-(1-phenylpropen-2-yl)cyclohexane-1-ol 
• 79090-75-8 (hydroxy-1 cyclohexyl)-3 phenyl-3 propadiene-1,2 

Relevant academic research and scientific papers

One-point binding ligands for asymmetric gold catalysis: Phosphoramidites with a TADDOL-related but acyclic backbone

Readily available phosphoramidites incorporating TADDOL-related diols with an acyclic backbone turned out to be excellent ligands for asymmetric gold catalysis, allowing a number of mechanistically different transformations to be performed with good to outstanding enantioselectivities. This includes [2 + 2] and [4 + 2] cycloadditions of ene-allenes, cycloisomerizations of enynes, hydroarylation reactions with formation of indolines, as well as intramolecular hydroaminations and hydroalkoxylations of allenes. Their preparative relevance is underscored by an application to an efficient synthesis of the antidepressive drug candidate (-)-GSK 1360707. The distinctive design element of the new ligands is their acyclic dimethyl ether backbone in lieu of the (isopropylidene) acetal moiety characteristic for traditional TADDOLs. Crystallographic data in combination with computational studies allow the efficiency of the gold complexes endowed with such one-point binding ligands to be rationalized.

Kinetic resolutions by enantioselective Pauson-Khand-type reaction

A kinetic resolution of 1-arylallyl propargyl ethers by enantioselective Pauson-Khand-type reaction catalysts was successfully carried out. While cationic rhodium(I) with a BINAP-based ligand having an electron-deficient phosphine is the choice for the sl

Intramolecular anionic Diels-Alder reactions of 1-aryl-4-oxahepta-1,6-diyne systems in DMSO

Base-promoted cycloaddition reactions of 1-aryl- or 1-aryl-7-substituted-4- oxahepta-1,6-diyne systems in DMSO have proven to involve an anionic intramolecular Diels-Alder process taking place even at room temperature in spite of the reaction suffering from temporary disruption of aromaticity. Although initially formed α-arylallenide anion can be protonated by DMSO, it can be back to the allenide anion probably because of a small acidity difference between α-arylallene and DMSO. The α-arylallenide anion in combination with the α-aryl substituent can constitute an anionic diene structure that undergoes the intramolecular Diels-Alder reaction involving the C(6)-yne part, a very fast process probably because of the increased HOMO-1 level of the anionic diene, as shown by DFT calculations. Diversified substituted naphthalenes, benzofurans, phenanthrenes, and quinolines, including biaryl architectures, are available from 4-oxahepta-1,6-diynes in a highly expeditious way.