235085-09-3

Upstream product

• 75359-71-6 4-phenylheptane-2,6-dione 
• 67-64-1 acetone 
• 122-57-6 1-Phenylbut-1-en-3-one 

Downstream Products

• 1431136-81-0 anti-(2S,3S,5S)-2,3-epoxy-3-methyl-5-phenylcyclohexanone 

Relevant academic research and scientific papers

Highly enantioselective Michael-aldol-dehydration reaction for the synthesis of chiral 3,5-diaryl-cyclohexenones catalyzed by primary amine

A simple organocatalytic Michael-aldol-dehydration domino approach to chiral 3,5-diaryl-cyclohexenones from acetone and α,β-unsaturated ketones was developed for the first time using a simple chiral primary amine as a catalyst. Moderate to good yields (up to 85%) and excellent enantioselectivities (88–98% ee) were obtained.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Primary-amine-catalyzed enantioselective intramolecular aldolizations

Aldol cyclodehydration of 4-substituted-2,6-heptanediones leads to enantiomerically enriched 5-substituted-3-methyl-2-cyclohexene-1-ones, which serve as perfume ingredients and valuable synthetic building blocks.Primary amines derived from cinchona alkalo