208922-82-1

Usage

General Description

2,5-Pyrrolidinedione, 1-cyclohexyl-3,4-dihydroxy-, (3R,4R)- (9CI), also known as D-(-)-dihydroxyphenylserine, is a chemical compound that consists of a cyclohexane ring with two hydroxyl groups attached, along with a pyrrolidinedione ring. It is classified as a chiral compound, with the (3R,4R) configuration. This chemical is often used in the synthesis of pharmaceuticals and agrochemicals, and it is also known for its potential biological activity. Additionally, it has been studied for its potential to act as an antioxidant and neuroprotective agent. Overall, 2,5-Pyrrolidinedione, 1-cyclohexyl-3,4-dihydroxy-, (3R,4R)- (9CI) is an important compound with various potential applications in the fields of medicine and chemistry.

Upstream product

• 87-69-4 L-Tartaric acid 
• 108-91-8 cyclohexylamine 

Downstream Products

• 880497-73-4 (3R,4R)-3,4-diamino-1-cyclohexylpyrrolidine 
• 1428558-82-0 (3R,4R)-N₃,N₄-bis[3,5-di-t-butylsalicylidene]-1-cyclohexyl-3,4-diaminopyrrolidine 
• 1428558-84-2 C₃₂H₃₃N₃O₂ 
• 209625-83-2 (3R,4R)-1-cyclohexyl-3,4-diacetoxypyrrolidine-2,5-dione 

Relevant academic research and scientific papers

(3S,4S)-N-substituted-3,4-dihydroxypyrrolidines as ligands for the enantioselective Henry reaction

The enantioselective Henry reaction is a very important and useful carbon–carbon bond forming reaction. The execution of this reaction requires the use of efficient chiral catalysts. In this work, in situ formed complexes of N-substituted dihydroxypyrrolidines, chiral ligands derived from L-tartaric acid and amines, were evaluated as catalysts in the enantioselective Henry reaction. The results showed that the nature of the N-substituent on the ligand significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, in the presence of DIPEA, for the reaction of aromatic aldehydes with nitromethane, at room temperature, originating products with er up to 92:8 (R:S) and conversions up to 96%. The interaction between the pyrrolidine ligand and the copper ion, in isopropanol, was followed by UV-vis spectrophotometry, showing a 1:1 stoichiometry and a binding constant of 4.4. The results obtained will contribute to the design and development of more efficient chiral catalysts for this type of reaction.

The synthesis of tetradentate salens derived from (3R,4R)-N-substituted-3, 4-diaminopyrrolidines and their application in the enantioselective trimethylsilylcyanation of aromatic aldehydes

The in situ formed Ti(IV) complexes of pyrrolidine-based chiral salen ligands derived from natural l-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of aromatic aldehydes. The different activity and selectivity of the catalysts in the formation of the products were found to be dependent on the N-substituent of the pyrrolidine.