42393-11-3

Upstream product

• 67-56-1 methanol 
• 33185-97-6 (E)-4-(4'-chlorophenyl)-2-oxo-3-buteneoic acid 
• 3395-81-1 4-chlorobenzaldehyde dimethyl acetal 
• 104-88-1 4-chlorobenzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 1000400-63-4 potassium 4-(4-chlorophenyl)-2-oxobut-3-enoate 
• 74-88-4 methyl iodide 

Downstream Products

• 105213-19-2 {3-[(E)-2-(4-Chloro-phenyl)-vinyl]-2-oxo-2H-benzo[1,4]oxazin-6-yl}-acetic acid methyl ester 
• 105213-25-0 2-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-2-oxo-2H-benzo[1,4]oxazin-6-yl}-propionic acid methyl ester 
• 1131450-65-1 methyl (S)-1-(4-chlorophenyl)-1H-benzo[f]chromene-3-carboxylate 
• 1171110-65-8 (R)-methyl 6-amino-4-(4-chlorophenyl)-5-cyano-4H-pyran-2-carboxylate 
• 1172623-51-6 (4S,4aR,8aR)-8a-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-4-(4-chlorophenyl)-4a,5,6,7,8,8a-hexahydro-4H-chromene-2-carboxylic acid methyl ester 
• 1172623-65-2 (4S,4aR,7aR)-7a-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-4-(4-chlorophenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[b]pyran-2-carboxylic acid methyl ester 
• 1217974-46-3 (2S,4R)-methyl-4-(4-chlorophenyl)-5-cyano-2-hydroxy-6-phenyl-3,4-dihydro-2H-pyran-2-carboxylate 
• 1210350-42-7 C₁₉H₁₆ClNO₃ 
• 1210054-91-3 C₁₈H₁₇ClO₅ 
• 1210054-92-4 C₁₉H₁₉ClO₅ 
• 1228393-35-8 trimethyl 2-(4-chlorophenyl)-4-oxobutane-1,1,4-tricarboxylate 
• 1257520-15-2 (4R,4aS,7aS)-methyl 4-(4-chlorophenyl)-4,4a,5,7a-tetrahydrocyclopenta[b]pyran-2-carboxylate 
• 1201890-26-7 methyl 2-((2S,3R)-3-(4-chlorophenyl)oxiran-2-yl)-2-oxoacetate 
• 1260498-01-8 methyl 2-(2-benzoyl-3-(4-chlorophenyl)cyclopropyl)-2-oxoacetate 

Relevant academic research and scientific papers

Asymmetric Catalytic Formal 1,4-Allylation of β,γ-Unsaturated α-Ketoesters: Allylboration/Oxy-Cope Rearrangement

A highly enantioselective formal conjugate allyl addition of allylboronic acids to β,γ-unsaturated α-ketoesters has been realized by employing a chiral NiII/N,N′-dioxide complex as the catalyst. This transformation proceeds by an allylboration/oxy-Cope rearrangement sequence, providing a facile and rapid route to γ-allyl-α-ketoesters with moderate to good yields (65–92 %) and excellent ee values (90–99 % ee). The isolation of 1,2-allylboration products provided insight into the mechanism of the subsequent oxy-Cope rearrangement reaction: substrate-induced chiral transfer and a chiral Lewis acid accelerated process. Based on the experimental investigations and DFT calculations, a rare boatlike transition-state model is proposed as the origin of high chirality transfer during the oxy-Cope rearrangement.

Facile synthesis of substituted diaryl sulfones: Via a [3 + 3] benzannulation strategy

A base-mediated [3 + 3] benzannulation strategy for the conversion of 1,3-bis(sulfonyl)propenes and β,γ-unsaturated α-ketoesters to diaryl sulfones has been developed. This method provides facile, metal-free and efficient access to highly substituted diaryl sulfones in good to excellent yields. In addition, the sulfonyl group could be easily removed or converted to other functional groups via an organostannane intermediate.

Boosting Chemical Stability, Catalytic Activity, and Enantioselectivity of Metal-Organic Frameworks for Batch and Flow Reactions

A key challenge in heterogeneous catalysis is the design and synthesis of heterogeneous catalysts featuring high catalytic activity, selectivity, and recyclability. Here we demonstrate that high-performance heterogeneous asymmetric catalysts can be engineered from a metal-organic framework (MOF) platform by using a ligand design strategy. Three porous chiral MOFs with the framework formula [Mn2L(H2O)2] are prepared from enantiopure phosphono-carboxylate ligands of 1,1′-biphenol that are functionalized with 3,5-bis(trifluoromethyl)-, bismethyl-, and bisfluoro-phenyl substituents at the 3,3′-position. For the first time, we show that not only chemical stability but also catalytic activity and stereoselectivity of the MOFs can be tuned by modifying the ligand structures. Particularly, the MOF incorporated with -CF3 groups on the pore walls exhibits enhanced tolerance to water, weak acid, and base compared with the MOFs with -F and -Me groups. Under both batch and flow reaction systems, the CF3-containing MOF demonstrated excellent reactivity, selectivity, and recyclability, affording high yields and enantioselectivities for alkylations of indoles and pyrrole with a range of ketoesters or nitroalkenes. In contrast, the corresponding homogeneous catalysts gave low enantioselectivity in catalyzing the tested reactions.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

A New Strategy for Enantioselective Construction of Multisubstituted Five-Membered Oxygen Heterocycles via a Domino Michael/Hemiketalization Reaction

A new highly enantioselective domino Michael/hemiketalization reaction of α-hydroxyacetophenone with β,γ-unsaturated α-keto esters for the synthesis of 2,2,4,5-tetrasubstituted chiral tetrahydrofurans is reported. With 2 mol% intramolecular dinuclear zinc

Synthesis of functionalized 2,5-dihydro-1,2-oxaphospholes via one-pot three-component reaction

An efficient one-pot synthesis of novel 2,5-dihydro-1,2-oxaphosphole derivatives via a three-component reaction of triphenyl phosphine, dialkyl acetylenedicarboxylates, and methyl (arylmethylidene) pyruvates has been reported. Carrying out the reaction in

Phosphine-catalyzed domino reactions: A route to functionalized bicyclic skeletons

A novel strategy that involves phosphine-catalyzed sequential [2+3] and [3+2] annulation reactions was developed. In this domino reaction, γ-substituted allenoates were used as novel C4 synthons, and the bicyclic cyclopenta[b]dihydrofuran derivatives were produced in good to excellent diastereoselectivities and yields under mild conditions. Furthermore, preliminary studies on an asymmetric variant of this reaction proceeded with moderate enantioselectivity.

Efficient enantioselective synthesis of dihydropyrans using a chiral N, N ′-dioxide as organocatalyst

The bifunctional organocatalyst C3 N,N′-dioxide has been successfully applied to the asymmetric cascade Michael/hemiacetalization reaction of α-substituted cyano ketones and β,γ-unsaturated α-ketoesters for the synthesis of multifunctionalized chiral dihydropyrans. The corresponding products were obtained in excellent yields (up to 99%) with high to excellent enantioselectivities (up to 99% ee).

Synthesis of polysubstituted 1,4-dihydropyridines via three-component reaction

An efficient one-pot synthesis of novel N-substituted 1,4-dihydropyridine derivatives via a threecomponent reaction of primary amines, dialkyl acetylenedicarboxylates, and methyl (arylmethylidene) pyruvates has been reported. The reaction is performed using ZnCl2 (40 mol %) in dichloroethane in good to high yields through a domino Michael/cyclization sequence. Notably, the ready availability of the starting materials, high bond-forming efficiency, good to high yields and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to Nsubstituted 1,4-dihydropyridines.

Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: Effect of substrate structure and mechanism

Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl α-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted α-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion.