153062-87-4Relevant articles and documents
Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope
Yan, Lu,Meng, Yan,Haeffner, Fredrik,Leon, Robert M.,Crockett, Michael P.,Morken, James P.
, p. 3663 - 3673 (2018/03/21)
A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.
Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes
Coombs, John R.,Haeffner, Fredrik,Kliman, Laura T.,Morken, James P.
supporting information, p. 11222 - 11231 (2013/08/23)
The Pt-catalyzed enantioselective diboration of terminal alkenes can be accomplished in an enantioselective fashion in the presence of chiral phosphonite ligands. Optimal procedures and the substrate scope of this transformation are fully investigated. Reaction progress kinetic analysis and kinetic isotope effects suggest that the stereodefining step in the catalytic cycle is olefin migratory insertion into a Pt-B bond. Density functional theory analysis, combined with other experimental data, suggests that the insertion reaction positions platinum at the internal carbon of the substrate. A stereochemical model for this reaction is advanced that is in line both with these features and with the crystal structure of a Pt-ligand complex.
One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates
Davies, Stephen G.,Fletcher, Ai M.,Kurosawa, Wataru,Lee, James A.,Poce, Giovanna,Roberts, Paul M.,Thomson, James E.,Williamson, David M.
experimental part, p. 7745 - 7756 (2011/01/05)
Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br 3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. When a solution of a secondary allylic or homoallylic amine and Br 3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one).