116760-89-5Relevant 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 α-branched enals
Lifchits, Olga,Reisinger, Corinna M.,List, Benjamin
supporting information; experimental part, p. 10227 - 10229 (2010/09/06)
An asymmetric catalytic epoxidation of α-branched, α,β-unsaturated aldehydes is presented. A highly synergistic combination of a primary cinchona-based amine and a chiral phosphoric acid was found to promote the reaction with excellent enantiocontrol for α-monosubstituted and α,β-disubstituted enals.
A STEREOSELECTIVE SYNTHESIS OF (Z)-α,β-DISUBSTITUTED ACRYLATES
Shimagaki, Masayuki,Shiokawa, Manabu,Sugai, Kazunori,Teranaka, Tomoko,Nakata, Tadashi,Oishi, Takeshi
, p. 659 - 662 (2007/10/02)
A new route for (Z)-α,β-disubstituted acrylate is described which is made up of 1) stereoselective reduction of ketones 3 and 2) conversion of the resulting syn-2 into (Z)-1.
