2031-37-0Relevant academic research and scientific papers
A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization
Li, Sifan,Wang, Yu,Wu, Zibo,Shi, Weiliang,Lei, Yibo,Davies, Paul W.,Shu, Wei
, p. 7209 - 7214 (2021/09/14)
Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.
Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization
Biosca, Maria,Eriksson, Lars,Hedberg, Martin,Himo, Fahmi,Lübcke, Marvin,Szabó, Kálmán J.,Wang, Qiang
supporting information, p. 20048 - 20057 (2020/11/27)
1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with in situ generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to investigate the details of the mechanism and the factors governing the stereoselectivity of the reaction.
