898539-35-0Relevant academic research and scientific papers
Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions
Rosen, Brandon R.,Ney, Joshua E.,Wolfe, John P.
supporting information; experimental part, p. 2756 - 2759 (2010/07/08)
The development of conditions that allow use of inexpensive aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification reactions is described. A catalyst composed of Pd(OAc)2 and S-Phos minimizes N-arylation of the substrate and prevents formation of mixtures of regioisomeric products. A number of heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated with this method.
Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations
Fritz, Jonathan A.,Wolfe, John P.
, p. 6838 - 6852 (2008/09/21)
A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.
A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas
Fritz, Jonathan A.,Nakhla, Josephine S.,Wolfe, John P.
, p. 2531 - 2534 (2007/10/03)
A new strategy for the preparation of substituted imidazolidin-2-ones in two steps from readily available N-allylamines is described. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-one p
