40541-42-2

Upstream product

• 547-65-9 α-methylene-γ-butyrolactone 
• 696-62-8 para-iodoanisole 
• 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 
• 123-11-5 4-methoxy-benzaldehyde 
• 1530-62-7 3-(4-methoxybenzylidene)-dihydrofuran-2(3H)-one 

Downstream Products

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

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.

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

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.

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

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