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Dynamic Kinetic Asymmetric Heck Reaction for the Simultaneous Generation of Central and Axial Chirality

AutorCarmona, José A.; Hornillos, Valentín ; Ramírez-López, Pedro; Ros, Abel ; Iglesias-Sigüenza, Javier; Gómez-Bengoa, Enrique; Fernández, Rosario; Lassaletta, José M.
Fecha de publicación2018
EditorAmerican Chemical Society
CitaciónJournal of the American Chemical Society 140: 11067- 11075 (2018)
ResumenA highly diastereo- A nd enantioselective, scalable Pd-catalyzed dynamic kinetic asymmetric Heck reaction of heterobiaryl sulfonates with electron-rich olefins is described. The coupling of 2,3-dihydrofuran or N-boc protected 2,3-dihydropyrrole with a variety of quinoline, quinazoline, phthalazine, and picoline derivatives takes place with simultaneous installation of central and axial chirality, reaching excellent diastereo- A nd enantiomeric excesses when in situ formed [Pd/DM-BINAP] was used as the catalyst, with loadings reduced down to 2 mol % in large scale reactions. The coupling of acyclic, electron-rich alkenes can also be performed using a [Pd/Josiphos ligand] to obtain axially chiral heterobiaryl α-substituted alkenes in high yields and enantioselectivities. Products from Boc-protected 2,3-dihydropyrrole can be easily transformed into N,N ligands or appealing axially chiral, bifunctional proline-type organocatalysts. Computational studies suggest that a β-hydride elimination is the stereocontrolling step, in agreement with the observed stereochemical outcome of the reaction.
URIhttp://hdl.handle.net/10261/173221
Identificadoresdoi: 10.1021/jacs.8b05819
issn: 1520-5126
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