173674-99-2

Upstream product

• 621-59-0 isovanillin 
• 137-43-9 Cyclopentyl bromide 
• 175165-63-6 2-Cyclopentyloxy-1-methoxy-4-vinyl-benzene 
• 67387-76-2 3-cyclopentyloxy-4-methoxybenzylaldehyde 
• 175165-65-8 [(S)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclobut-1-enyloxy]-triethyl-silane 
• 175165-64-7 3-(3-Cyclopentyloxy-4-methoxy-phenyl)-cyclobutanone 

Downstream Products

• 85416-75-7 (R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one 
• 175165-66-9 (R)-3-(3-Cyclopentyloxy-4-methoxy-phenyl)-4-hydroxy-butyric acid methyl ester 
• 175165-67-0 (R)-4-Azido-3-(3-cyclopentyloxy-4-methoxy-phenyl)-butyric acid methyl ester 

Relevant academic research and scientific papers

Intermolecular enantioselective Heck-Matsuda arylations of acyclic olefins: Application to the synthesis of β-aryl-γ-lactones and β-aryl aldehydes

We describe herein a synthetically useful method for the enantioselective intermolecular Heck-Matsuda arylation of acyclic allylic alcohols. Aryldiazonium tetrafluoroborates were applied as arylating agents in the presence of Pd(TFA)2 and a chiral, commercially available, bisoxazoline ligand. The methodology is straightforward, robust, scalable up to a few grams, and of broad scope allowing the synthesis of a range of β-aryl-carbonyl compounds in good to high enantioselectivities and yields. This new enantioselective Heck-Matsuda arylation allowed the synthesis of β-aryl-γ-lactones and β-aryl aldehydes, which play a vital role as key intermediates in the synthesis of the biologically active compounds, such as (R)-baclofen, (R)-rolipram, (S)-curcumene, (S)-dehydrocurcumene, and (S)-tumerone.

Chiral synthesis of phosphodiesterase inhibitor, (R)-(-)-rolipram, by means of enantioselective deprotonation strategy

Enantioselective synthesis of the antidepressant (R)-(-)-rolipram (1) has been achieved by using an enantioselective deprotonation of the cyclobutanone derivative as a key step.