10436-86-9

Upstream product

• 91266-26-1 (Z)-5-Methoxy-5-phenyl-pent-4-enoic acid methyl ester 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 2327-99-3 1-phenylpropadiene 
• 201230-82-2 carbon monoxide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 16277-67-1 3-methoxy-1-phenylpropene 
• 1428901-66-9 C₁₆H₂₀O₄ 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 292638-85-8 acrylic acid methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 186581-53-3 diazomethane 
• 2628-87-7 2-phenylglutaric acid 

Downstream Products

• 101999-42-2 (+/-)-2-phenyl-1,5-pentanediol 
• 56523-53-6 dimethyl (S)-2-phenylglutarate 
• 56523-52-5 dimethyl (R)-2-phenylglutarate 

Relevant academic research and scientific papers

Synthesis of chiral pentacyclo-undecane macrocycles and their use in enantioselective Michael addition reactions

The synthesis of a new class of chiral cage annulated macrocycles with C1 symmetry and five donor atoms is reported. The cage annulated hosts catalysed the addition of 2-nitropropane to chalcone with high enantioselectivities (up to 92% ee) but

Asymmetric Michael addition and deracemization of enolate by chiral crown ether

Crown ethers anellated to glucose units have been used to catalyse the enantioselective Michael addition of methyl phenylacetate to methyl acrylate in high chemical yields in up to 84% enantiomeric excess. A novel CH-acid deracemization has also been disc

Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters

The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.

Hydrogen-Bonding Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers over Ionic Liquid under Metal-Free Conditions

O-heterocycles have wide applications, and their efficient and green synthesis is very interesting. Herein, we report hydrogen-bonding catalyzed ring-closing metathesis of aliphatic ethers to O-heterocycles over ionic liquid (IL) catalyst under metal- and solvent-free conditions. The IL 1-butylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3H-BMIm][OTf]) is discovered to show outstanding performance, better than the reported catalysts. An interface effect plays an important role in mediating the reaction rate due to the immiscibility between the products and the IL catalyst, and the products can be spontaneously separated. NMR analysis and DFT calculation suggest that a pair of cation and anion of [SO3H-BMIm][OTf] could form three strong H-bonds with an ether molecule, which catalyze the ether transformation via a cyclic oxonium intermediate. A series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines and dioxane can be obtained from their corresponding ethers in excellent yields (e.g., >99 %). This work opens an efficient and metal-free way to produce O-heterocycles from aliphatic ethers.

PROCESS FOR DOUBLE CARBONYLATION OF ALLYL ALCOHOLS TO CORRESPONDING DIESTERS

The invention relates to a process for doubly carbonylating allyl alcohols to the corresponding diesters, wherein a linear or branched allyl alcohol is reacted with a linear or branched alkanol (alcohol) with supply of CO and in the presence of a catalytic system composed of a palladium complex and at least one organic phosphorus ligand and in the presence of a hydrogen halide selected from HCl, HBr and HI.

PROCESS FOR DOUBLE CARBONYLATION OF ALLYL ETHERS TO CORRESPONDING DIESTERS

The invention relates to a process for doubly carbonylating allyl ethers to the corresponding diesters, wherein a linear or branched allyl ether is reacted with a linear or branched alkanol (alcohol) with supply of CO and in the presence of a catalytic system composed of a palladium complex and at least one organic phosphorus ligand and in the presence of a hydrogen halide selected from HCl, HBr and HI.

First iodine-catalyzed deallylation of reactive allyl methylene esters

C-Allyl cleavage has been developed using the inexpensive and mild reagent iodine in dimethylsulfoxide. A variety of compounds with active methylene groups were C-deallylated using this reagent. This method is efficient and operationally simple in comparison to the methods using transition-metal complexes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Stereocontrol in radical cyclization: Change in rate-determining step

Intramolecular cyclization of an α-carbon radical of ester carrying a chiral 2,4-pentanediol tether shows low stereoselectivity when the radical carbon has an alkyl substituent, while the selectivity becomes high to give a single stereoisomer (>99% pure)

Oxidative rearrangements of arylalkanones with 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide, a 'green' analog of Koser's reagent

Previous methods for the conversion of arylalkanones to alkyl 2-arylesters by oxidative rearrangement utilized reagents which either produced toxic metal salts or halogenated organics as by-products. In this report, 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-dioxide (HMBI) is used to effect this useful transformation, where the reduced iodine reagent is water-soluble and readily recycled.

CROWN ETHERS AS ENZYME MODELS FOR A CHIRAL C-C BOND FORMATION REACTION

Optically active crown ethers tuned with steric and micro-environmental features catalyse the Michael addition of methyl phenylacetate to methyl acrylate to give a chiral product with predictable configuration.The mechanistic rational of the chiral induct