97080-09-6

Upstream product

• 1963-36-6 4-methoxycinnamaldehyde 
• 97116-47-7 racem.-3.4-bis-(4-methoxy-phenyl)-adipic acid dimethyl ester 
• 97116-47-7 meso-3.4-bis-(4-methoxy-phenyl)-adipic acid dimethyl ester 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 

Downstream Products

• 94311-36-1 trans-3,4-Bis-(4-methoxy-phenyl)-cyclopentanon-⁽¹⁾-oxim 

Relevant academic research and scientific papers

Oxidatively initiated NHC-catalyzed enantioselective synthesis of 3,4-disubstituted cyclopentanones from enals

An unprecedented N-heterocyclic carbene (NHC)-catalyzed annulation of enals to form 3,4-disubstituted cyclopentanones has been discovered. Aryl enals undergo dimerization in the presence of a single-electron oxidant to form C2 symmetric cyclopentanones. A cross-reaction has also been developed, allowing for the synthesis of differentially substituted cyclopentanones. Mechanistically, the reaction is thought to proceed through radical intermediates, further establishing the synthetic utility of this class of reactivity.

Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: Application to asymmetric synthesis of hydrodimers

The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58-90% de). In all cases, small amounts (2-symmetric dl-3,4-diaryladipic acids and trans-3,4-diarylcyclopentanones. The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, prepared from (1R)-(+)-camphor, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.