17488-76-5

Upstream product

• 76772-95-7 dl-cis-ethyl methyl cyclohexane-1,2-dicarboxylate 
• 64-17-5 ethanol 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 17488-76-5 (1S,2R)-Cyclohexane-1,2-dicarboxylic acid monoethyl ester 

Downstream Products

• 76772-95-7 dl-cis-ethyl methyl cyclohexane-1,2-dicarboxylate 
• 17488-76-5 C₁₀H₁₆O₄ 
• 275815-60-6 (1R,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde 
• 275812-32-3 N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N'-((1R,2S)-2-{[3(S)-(4-fluorobenzyl)piperidinyl]methyl}cyclohexyl)urea 
• 213672-84-5 trans-(1R,2R)-1-(benzyloxycarbonylamino)-2-hydroxymethyl-cyclohexane 

Relevant academic research and scientific papers

Heterogeneous organocatalysis for the asymmetric desymmetrization of meso-cyclic anhydrides using silica gel-supported bis-cinchona alkaloids

The silica gel-supported bis-cinchona alkaloid 1a was prepared and found to be an efficient heterogeneous chiral organocatalyst with high catalytic activities, enantioselectivities (up to 92% ee), and recyclability for the asymmetric desymmetrization of m

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.

A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists

A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.

An efficient approach for the deprotection of esters using ionic liquid as nucleophile

An efficient approach for the deprotection of esters has been developed using ionic liquid as nucleophile in the presence of protic acid. Using methyl benzoate as a model compound, the best result was obtained by the combination of 1-methylimidazolium bromide and methane sulfonic acid with a conversion of 96 % after 2 h at 120 C.

Stereoselective process for a CCR3 antagonist

A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Anoth

Ring opening of cyclic anhydrides: Synthesis of achiral half-esters using Lewis acids

A rapid and high yield preparation of half-esters from cyclic anhydrides using alcohols and Lewis acids is described.

Hard Acid and Soft Nucleophile Systems. 3.1 Dealkylation of Esters with Aluminum Halide-Thiol and Aluminum Halide-Sulfide Systems

Benzyl and methyl esters of aliphatic and aromatic carboxylic acids have been easily cleaved on treatment with aluminum halide and ethanethiol to give parent carboxylic acids in quantitative yields.A new combination of aluminum halide with dialkyl sulfide has been found to make up a powerful deesterification reagent system useful for general esters.