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• 22748-16-9 4,4-dimethylcyclopent-2-ene-1-one 

Relevant academic research and scientific papers

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.

Catalytic asymmetric epoxidation of 2-cyclopentenones

The first highly efficient asymmetric epoxidation of 2-cyclopentenones has been developed. Using a newly designed and readily available Cinchona amine catalyst, 2-cyclopentenones are reacted with hydrogen peroxide to give the corresponding epoxycyclopentanones in high yields and excellent enantioselectivities. Copyright

Lithium naphthalenide induced reductive cleavage of α,β-epoxy ketones: An efficient procedure for the preparation of β-hydroxy ketones

Lithium naphthalenide presents itself as a mild and efficient reagent for the cleavage of α,β-epoxy ketones to give the corresponding β-hydroxy ketones in good yields.