83665-66-1Relevant academic research and scientific papers
Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes
Mennie, Katrina M.,Banik, Steven M.,Reichert, Elaine C.,Jacobsen, Eric N.
supporting information, p. 4797 - 4802 (2018/04/17)
The stereoselective synthesis of syn-β-fluoroaziridine building blocks via chiral aryl iodide-catalyzed fluorination of allylic amines is reported. The method employs HF-pyridine as a nucleophilic fluoride source together with mCPBA as a stoichiometric oxidant, and affords access to arylethylamine derivatives featuring fluorine-containing stereocenters in high diastereo- and enantioselectivity. Catalyst-controlled diastereoselectivity in the fluorination of chiral allylic amines enabled the preparation of highly enantioenriched 1,3-difluoro-2-amines bearing three contiguous stereocenters. The enantioselective catalytic method was applied successfully to other classes of multifunctional alkene substrates to afford anti-β-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.
Palladium-catalyzed regioselective and stereoselective oxidative heck arylation of allylamines with arylboronic acids
Zhang, Lingjuan,Dong, Chaonan,Ding, Chenjun,Chen, Jing,Tang, Weijun,Li, Huanrong,Xu, Lijin,Xiao, Jianliang
supporting information, p. 1570 - 1578 (2013/06/27)
A general and convenient palladium-catalyzed oxidative Heck arylation of both N-protected and N,N-diprotected allylic amines with arylboronic acids under mild conditions has been developed. The catalyst system, consisting of Pd(OAc)2 (palladium acetate), AgOAc (silver acetate) and KHF 2 (potassium hydrogen fluoride), could efficiently catalyze the coupling reaction in acetone without the aid of any ligand, leading exclusively to the γ-arylated allylic amine products in good to excellent yields. This method is highlighted with excellent regio- and stereocontrol and remarkable functional group tolerance. The carbamate moiety in allylic amine substrates is of crucial importance to the catalytic performance, and the chelation between the carbonyl O (oxygen) and Pd (palladium) atoms is believed to be responsible for the high regioselectivity and stereoselectivity observed. Copyright
