93603-11-3

Upstream product

• 67-56-1 methanol 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 7500-55-2 dimethyl cyclohex-4-ene-1,2-dicarboxylate 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 2305-26-2 cis-1,2,3,6-tetrahydrophthalic acid 
• 85-43-8 1,2,3,6-Tetrahydrophthalic anhydride 

Downstream Products

• 104265-85-2 C-((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methylamine; compound with (1R,2S)-cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester 
• 104265-86-3 (1R-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester 
• 91259-90-4 (1S,6R)-6-Benzyloxycarbonylamino-cyclohex-3-ene-1-carboxylic acid methyl ester 
• 88586-05-4 (1S,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester; compound with (1S,2S)-2-methylamino-1-phenyl-propan-1-ol 
• 88586-05-4 (1R,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester; compound with (1S,2S)-2-methylamino-1-phenyl-propan-1-ol 
• 104265-84-1 C-((1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methylamine; compound with (1S,2R)-cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester 
• 31139-02-3 (1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 
• 104265-90-9 (1S,6R)-Methyl 6-Hydroxymethyl-3-cyclohexene-1-carboxylate 
• 104265-88-5 (1R-cis)-6-Hydroxymethyl-3-cyclohexen-1-carbonsaeure-methylester 
• 93531-06-7 (1S,6R)-6-Chlorocarbonyl-cyclohex-3-enecarboxylic acid methyl ester 
• 150024-72-9 dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate 
• 91280-46-5 tert-butyl (1S,6S)-6-methoxycarbonylaminocyclohex-3-enecarboxylate 
• 820993-73-5 (1R,6S)-6-Azidocarbonyl-cyclohex-3-enecarboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

The New Catalyst System: Chloramphenicol Base and Organic Acid Co-catalyzed Enantioselective Alcoholysis of meso-Anhydride

In this study, the synergistic catalytic strategy was developed, which chloramphenicol base and organic acid were used in the same system, the optimal enantioselectivity value and yield (96% yield; 65% ee) was achieved using the binary co-catalyst in the asymmetric alcoholysis reaction of mesoanhydride. Moreover, a hypothetical intermediate between the substrate and the binary co-catalyst which is responsible for stereochemistry control in this catalytic reaction was proposed. In addition, the results of molecular mechanics calculations also have shed light on the corresponding catalytic mechanism.

Ionic Liquid Gels: Supramolecular Reaction Media for the Alcoholysis of Anhydrides

The search of new enantioselective catalysts, able to promote synthetically useful organic reactions with high levels of asymmetric induction, should be associated with the attention to the suitable reaction medium able to achieve the best efficiency in c

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

Enantioselective acyl-transfer catalysis by fluoride ions

The asymmetric nucleophilic catalysis by fluoride ions at a carbon-based electrophile has been demonstrated for the first time. Using a library of ad hoc designed bifunctional phase-transfer catalysts in which both the anion and the cation are directly involved in the reaction, the desymmetrisation of meso-succinic and -glutaric anhydrides is possible.19F NMR spectroscopic studies support the intermediacy of an acyl fluoride intermediate.

Reversible Switching and Recycling of Adaptable Organic Microgel Catalysts (Microgelzymes) for Asymmetric Organocatalytic Desymmetrization

Adaptable enzyme-mimetic catalysts based on temperature-responsive polymer microgels (microgelzymes) have been developed. By a simple change in the temperature, a microgel catalyst can be reversibly switched into its soluble or precipitated form, thus com

Scoping the Enantioselective Desymmetrization of a Poorly Water-Soluble Diester by Recombinant Pig Liver Esterase

Previously, the biocatalytic desymmetrization of dimethyl cyclohex-4-ene-cis-1,2-dicarboxylate to (1S,2R)-1-(methoxycarbonyl)cyclohex-4-ene-2-carboxylic acid, an important intermediate toward the synthesis of biologically active molecules, had been well-c

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.

Asymmetric synthesis of cis-4a,5,8,8a-tetrahydrophthalazin-1(2H)-one derivatives based on organocatalytic alcoholysis of cyclic dicarboxylic anhydride

Asymmetric synthesis of optically active cis-4-phenyl-4a,5,8,8atetrahydrophthalazin-1(2H)-one and its N-alkylated derivatives based on an organocatalytic enantioselective alcoholysis of cyclic dicarboxylic anhydride was described.

Desymmetrization of acid anhydride with asymmetric esterification catalyzed by chiral phosphoric acid

Asymmetric desymmetrization of σ-symmetric acid anhydrides was achieved with chiral phosphoric acid as a Br?nsted acid catalyst. The key of success was finding of benzhydrol and 2,2-diphenylethanol as the nucleophiles of choice. The corresponding half esters were obtained in good yields with high selectivity.

Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of meso Cyclic Anhydrides

The synthesis of new chloramphenicol-base-derived thiourea organocatalysts, (1S,2R)-12 a–f and (1R,2R)-15 a–c, and their use in the enantioselective alcoholysis of meso-anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)-12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)-15 a–c. This technique was used to synthesize (R)-(?)-baclofen.