40541-42-2

Upstream product

• 1530-62-7 3-(4-methoxybenzylidene)-dihydrofuran-2(3H)-one 
• 547-65-9 α-methylene-γ-butyrolactone 
• 696-62-8 para-iodoanisole 
• 123-11-5 4-methoxy-benzaldehyde 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 96-48-0 4-butanolide 
• 2746-25-0 p-Methoxybenzyl bromide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1301601-43-3 4-((4-methoxybenzyl)oxy)-1-(pyrrolidin-1-yl)butan-1-one 

Downstream Products

• 131188-84-6 3-(4-Methoxy-benzyl)-4-methyl-pentane-1,4-diol 
• 131188-86-8 4-Ethyl-3-(4-methoxy-benzyl)-hexane-1,4-diol 
• 1384881-69-9 3-(4-methoxybenzyl)pent-4-en-1-ol 
• 1384881-87-1 (Z)-3-(4-methoxybenzyl)-5-deuteropent-4-en-1-ol 

Relevant academic research and scientific papers

Palladium-catalysed vinylic substitution of aryl/vinyl iodides and triflates with α-methylene-γ-butyrolactone - An application to the synthesis of 3-alkyl-γ-butyrolactones through combined palladium-catalysed coupling/hydrogenation reactions

The palladium-catalysed arylation/vinylation of α-methylene-γ-butyrolactone (1) proceeds in good yield, mainly to give stereodefined aryl/vinyl-substituted α-alkylidene-γ-butyrolactones 4. In addition, the palladium-catalysed arylation of α-methylene-γ-bu

Palladium-catalyzed arylation of α-methylene-γ-butyrolactone: 3-benzylfuran-2(5H)-ones vs (Z)-benzylidene-γ-butyrolactones and their reduction to 3-benzyl-γ-butyrolactones

(formula presented) The palladium-catalyzed arylation of the α-methylene-γ-butyrolactone proceeds in good yields and may be directed toward the synthesis of 3-benzylfuran-2(5H)-ones when the starting aryl iodides contain strongly electron-withdrawing grou

Systematic Investigation into the Matsuda-Heck Reaction of α-Methylene Lactones: How Conformational Constraints Direct the β-H-Elimination Step

α-Methylene-γ-butyrolactone and α-methylene-δ-valerolactone undergo Pd-catalyzed Matsuda-Heck couplings with arene diazonium salts to α-benzyl butenolides or pentenolides, respectively, or to α-benzylidene lactones. The observed regioselectivity is strongly ring size dependent, with six-membered rings giving exclusively α-benzyl pentenolides, whereas the five-membered α-methylene lactone reacts to mixtures of regioisomers with a high proportion of (E)-α-benzylidene-γ-butyrolactones. DFT calculations suggest that the reasons for these differences are not thermodynamic but kinetic in nature. The relative energies of the conformers of the Pd σ-complexes resulting from insertion into the Pd-aryl bond were correlated with the dihedral angles between Pd and endo-β-H. This correlation revealed that in the case of the six-membered lactone an energetically favorable conformer adopts a nearly synperiplanar Pd/endo-β-H arrangement, whereas for the analogous Pd σ-complex of the five-membered lactone the smallest Pd/endo-β-H dihedral angle is observed for a conformer with a comparatively high potential energy. The optimized conditions for Matsuda-Heck arylations of exo-methylene lactones were eventually applied to the synthesis of the natural product anemarcoumarin A.

Copper-catalyzed intramolecular alkene carboetherification: Synthesis of fused-ring and bridged-ring tetrahydrofurans

Fused-ring and bridged-ring tetrahydrofuran scaffolds are found in a number of natural products and biologically active compounds. A new copper-catalyzed intramolecular carboetherification of alkenes for the synthesis of bicyclic tetrahydrofurans is reported herein. The reaction involves Cu-catalyzed intramolecular addition of alcohols to unactivated alkenes and subsequent aryl C-H functionalization provides the C-C bond. Mechanistic studies indicate a primary carbon radical intermediate is involved and radical addition to the aryl ring is the likely C-C bond-forming mechanism. Preliminary catalytic enantioselective reactions are promising (up to 75% ee) and provide evidence that copper is involved in the alkene addition step, likely through a cis-oxycupration mechanism. Catalytic enantioselective alkene carboetherification reactions are rare and future development of this new method into a highly enantioselective process is promising. During the course of the mechanistic studies a protocol for alkene hydroetherification was also developed.

Regioselective lactonization of unsymmetrical 1,4-diols: An efficient access to lactone lignans

A Cp*Ru-based bifunctional catalyst system (Cp* = η5-C5(CH3)5) with a suitably-designed PN ligand (PN = chelating tertiary phosphine-protic amine ligand) has been developed for a regioselective lactonization of

Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand

A novel catalytic method for the straightforward hydrogenation of carboxamides and esters to primary alcohols has been developed. Chiral modification in the ligand sphere of the well-defined Cp*Ru catalyst molecule opens up a new possibility for the development of an enantioselective hydrogenation of racemic substrates via dynamic kinetic resolution.

Steering reaction pathways: From benzyl Claisen rearrangements to powerful ionic shifts

Take a walk on the wild side: A novel benzyl Claisen cascade rearrangement of keteniminium salts is described. The reaction leads to α-arylated lactones under metal-free conditions (top scheme; Tf=trifluoromethanesulfonyl). It is further demonstrated that the cationic intermediates involved can be steered away from pericyclic reaction manifolds into powerful ionic shifts through reaction design (bottom scheme). Copyright

3-(Arylmethyl)-1-(3'-diethylaminopropyl) pyrrolidines and process of preparation thereof

The novel compounds 3-(arylmethyl)-1-(3'-diethylaminopropyl) pyrrolidines are disclosed which have the general formula: wherein R represents an alkoxy group having 1 to 6 carbon atoms, like methoxy, ethoxy, propoxy or butoxy and a process for preparing th