865366-99-0

Upstream product

• 137310-15-7 dimethyl 3-(p-chlorophenyl)glutarate 
• 67-56-1 methanol 
• 53911-68-5 3-(4-chlorophenyl)glutaric anhydride 
• 35271-74-0 3-(4-chlorophenyl)pentane-1,5-dioic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 20754-21-6 methyl 3-(4-chlorophenyl)propenoate 
• 137310-14-6 trimethyl 2-(4-chlorophenyl)propane-1,1,3-tricarboxylate 

Downstream Products

• 1186588-18-0 C₁₃H₁₆ClNO₄ 
• 63701-55-3 (R)-(-)-baclofen hydrochloride 

Relevant academic research and scientific papers

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.

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.

An efficient synthesis of (R)- and (S)-baclofen via desymmetrization

A short and highly enantioselective synthesis of both enantiomers of GABA agonist baclofen in four steps with total yields of 32.8% [for (S)-isomer] and 35.1% [for (R)-isomer] is reported. The key step involved desymmetrization of cyclic anhydride with mo

Enzymatic desymmetrization of 3-arylglutaric acid anhydrides

Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4.

Chemoenzymatic synthesis of both enantiomers of baclofen

Both enantiomers of baclofen have been synthesized in five steps from 4-chlorocinnamic acid. The key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin.