RT Journal Article
T1 Chiral Ligands Based on Binaphthyl Scaffolds for Pd-Catalyzed Enantioselective C–H Activation/Cycloaddition Reactions
A1 González González, José Manuel
A1 Vidal Pereira, Xandro
A1 Ortuño Maqueda, Manuel Ángel
A1 Mascareñas Cid, José Luis
A1 Gulías Costa, Moisés
K1 Allenes
K1 Annulations
K1 Chemical structure
K1 Ligands
K1 Stereoselectivity
AB 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
PB ACS Publications
SN 0002-7863
YR 2022
FD 2022
LK http://hdl.handle.net/10347/29687
UL http://hdl.handle.net/10347/29687
LA eng
NO J. Am. Chem. Soc. 2022, 144, 47, 21437–21442
NO This work received financial support from the MCIN/AEI/10.13039/501100011033 (Projects PID2019-108624RB-I00, PID2019-110385GB-I00, and PID2020-119116RA-I00 and FPU Fellowship to X.V.), the Consellería de Cultura, Educación e Ordenación Universitaria (ED431C-2021/25, ED431G 2019/03: Centro Singular de Investigación de Galicia accreditation 2019–2022, and fellowship to J.M.G.), and the European Regional Development Fund (ERDF). The orfeo-cinqa network CTQ2016-81797-REDC is also kindly acknowledged. M.A.O. acknowledges the Xunta Distinguished Researcher Program (ED431H 2020/21) for funding and Centro de Supercomputación de Galicia (CESGA) for providing generous computational resources. Figures were created with CYLview20
DS Minerva
RD 23 abr 2026