Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.
Dinis Veloso Guerreiro, Miguel
KAUST DepartmentChemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2019-11-08
Print Publication Date2019-12-11
Embargo End Date2020-11-09
Permanent link to this recordhttp://hdl.handle.net/10754/660479
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AbstractA series of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100-500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands in asymmetric catalysis. Isolation and comprehensive characterization of the reaction intermediates support a catalysis cycle proposed by DFT calculations.
CitationLebedev, Y., Polishchuk, I., Maity, B., Dinis Veloso Guerreiro, M., Cavallo, L., & Rueping, M. (2019). Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis. Journal of the American Chemical Society. doi:10.1021/jacs.9b10364
SponsorsB.M. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.
PublisherAmerican Chemical Society (ACS)
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