1383979-37-0Relevant academic research and scientific papers
The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide
Lifchits, Olga,Mahlau, Manuel,Reisinger, Corinna M.,Lee, Anna,Fares, Christophe,Polyak, Iakov,Gopakumar, Gopinadhanpillai,Thiel, Walter,List, Benjamin
supporting information, p. 6677 - 6693 (2013/06/05)
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
Lee, Anna,Reisinger, Corinna M.,List, Benjamin
supporting information; experimental part, p. 1701 - 1706 (2012/07/30)
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
