379679-67-1

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 379679-62-6 3-bromo-2-(4-fluorophenyl)-2-cyclopenten-1-one 
• 14203-25-9 2-bromo-3-methoxy-cyclopent-2-en-1-one 
• 1765-93-1 4-fluoroboronic acid 
• 379679-70-6 2-(4-fluorophenyl)-1,3-cyclopentanedione 
• 5870-62-2 3-hydroxy-2-cyclopenten-1-one 

Downstream Products

• 459174-07-3 (S)-(-)-methyl 2-(4-fluorophenyl)-3-hydroxycyclopent-1-enecarboxylate 
• 405512-96-1 (1S,2R,3R)-2-(4-fluorophenyl)-3-hydroxymethylcyclopentanol 
• 190269-75-1 methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate 
• 459174-01-7 2-(4-fluoro-phenyl)-2,3-dihydroxy-cyclopentanone 
• 379679-64-8 methyl 2-(4-fluorophenyl)-3-oxo-1-cyclopent-1-enecarboxylate 
• 379679-62-6 3-bromo-2-(4-fluorophenyl)-2-cyclopenten-1-one 
• 379679-70-6 2-(4-fluorophenyl)-1,3-cyclopentanedione 

Relevant academic research and scientific papers

Asymmetric synthesis of 1,2,3-trisubstituted cyclopentanes and cyclohexanes as key components of substance P antagonists

An efficient asymmetric synthesis of 1,2,3-trisubstituted cyclopentanes and cyclohexanes is described. Three methods were developed for the preparation of the 2,3-disubstituted cyclopentenones and cyclohexenones, which are key achiral building blocks. These intermediates are reduced catalytically with (R)-2-methyloxazaborolidine in high yield (82-98%) and excellent ee (89-96%). Directed reduction of the chiral allylic alcohols using Red-Al gives exclusively the 1,2-anti stereochemistry (>99:1). Epimerization of the ester center followed by saponification/crystallization affords the desired hydroxyacids in good yield (65-70%) and in high enantiomeric excess (>99%).