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Chiral Ligands Based on Binaphthyl Scaffolds for Pd-Catalyzed Enantioselective C–H Activation/Cycloaddition Reactions

2022; American Chemical Society; Volume: 144; Issue: 47 Linguagem: Inglês

10.1021/jacs.2c09479

1943-2984

José Manuel González, Xandro Vidal, Manuel Á. Ortuño, José L. Mascareñas, Moisés Gulı́as,

Cyclopropane Reaction Mechanisms

We report the first examples of the use of a new class of ligands (NOBINAc) for performing asymmetric C-H activations using palladium catalysts. These ligands combine the axial chirality of binaphthyl scaffolds with the bifunctional and bidentate coordination properties of mono-N-protected amino acids (MPAAs), which are well-known to favor Pd-promoted C-H activations via concerted metalation-deprotonation mechanisms. We demonstrate that our new ligands enable substantially higher enantioselectivities than MPAAs in the assembly of 2-benzazepines through formal (5 + 2) cycloadditions between homobenzyltriflamides or o-methylbenzyltriflamides and allenes.