56523-53-6

Upstream product

• 59349-80-3 (S)-2-phenyl-glutaric acid 
• 292638-85-8 acrylic acid methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 2628-87-7 2-phenylglutaric acid 
• 10436-86-9 dimethyl 2-phenylpentanedioate 

Downstream Products

• 1239919-68-6 (S)-2-phenylpentane-1,5-diol 
• 52937-63-0 D-2-phenyl-pentane 
• 103169-76-2 (S)-2-phenyl-1,5-bis-(toluene-4-sulfonyloxy)-pentane 

Relevant academic research and scientific papers

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)

Transformation of linear oligoketosides into macrocyclic neoglycoconjugates

The macrocyclization of linear d-galacto-2-heptulopyranose-containing oligoketosides has been carried out by intramolecular glycosidation and ring-closing metathesis. The aglycon fragment of the cyclic neglycoconjugates thus formed was an alkylidene or a

Enantioselective Michael addition catalyzed by chiral tripodal oxazoline-tBuOK complexes

Benzene-based tripodal oxazolines are found to be novel chiral ligands for the catalytic enantioselective Michael addition via potassium enolates. Thus, methyl phenylacetate undergoes 1,4-addition to methyl acrylate using a catalytic amount of a tBuOK-oxa

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

Asymmetric Michael reaction. Deracemization of enolate by chiral crown ether

Crown ethers anellated to sugar units have been used to catalyse the enantioselective carbon-carbon bond forming reaction of methyl phenylacetate with methyl acrylate. A novel CH-acid deracemization has also been discovered in this study.

New chiral crown ethers derived from camphor and their application to asymmetric Michael addition. First attempts to rationalize enantioselection by AM1 and AMBER calculations

The synthesis of novel optically active crown ethers derived from (1R)- (+)-camphor is described. The mechanism of their catalytic effect upon the Michael addition of phenylacetate to acrylate is discussed in terms of kinetic vs. thermodynamic control in

Chiral Lithium 2-Aminoalkoxides as Reagents for Enantioselective Michael Reaction

Chiral lithium alkoxides were designed and applied to enantioselective Michael reaction of methyl phenylacetate and methyl acrylate to give the corresponding adduct in enantiomeric excess up to 84percent.The catalytic enantioselective Michael reaction is

Applications of Phase-Transfer Catalysis, 55. - New Experiments towards Enantioselective Phase-Transfer Catalysis with Optically Active Crown Ethers

Optically active crown ethers 1a - 1o, 2, 3a, b, 4a, b, 5a - 5d, 6a, b and the acyclic analogue 7 were used for three Michael-type additions, benzoin condensation, a C-alkylation, a base-catalyzed autoxidation and a hypochlorite epoxidation.Important obse

NEW SYNTHETIC STRATEGY TO HIGHLY SYMMETRIC CHIRAL MACROCYCLES FROM CARBOHYDRATE DERIVATIVES

A simple strategy for the synthesis of highly symmetric macrocycles incorporating carbohydrates is presented.The application of this strategy to the synthesis of optically active tetra-gluco-24-crown-8 (1), bis-gluco-15-crown-5 (3), and bis-gluco-21-crown

SIMPLE CHIRAL CROWN ETHERS COMPLEXED WITH POTASSIUM TERT-BUTOXIDE AS EFFICIENT CATALYSTS FOR ASYMMETRIC MICHAEL ADDITIONS

Simple C2-symmetric chiral crown ether 1 complexed with KOtBu was found to work as an efficient chiral catalyst in Michael additions to cause high asymmetric induction.The results with various chiral crown ethers as catalysts suggest that diaxial-like conformation of the vicinal methyl groups of 1potassium enolate complex is responsible for the chiral induction.