Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.
Type
ArticleAuthors
Lebedev, Yury
Polishchuk, Iuliia

Maity, Bholanath

Dinis Veloso Guerreiro, Miguel

Cavallo, Luigi

Rueping, Magnus

KAUST Department
Chemical Science ProgramKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2019-11-08Online Publication Date
2019-11-08Print Publication Date
2019-12-11Embargo End Date
2020-11-09Permanent link to this record
http://hdl.handle.net/10754/660479
Metadata
Show full item recordAbstract
A 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.Citation
Lebedev, 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.9b10364Sponsors
B.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.Publisher
American Chemical Society (ACS)Additional Links
https://pubs.acs.org/doi/10.1021/jacs.9b10364Relations
Is Supplemented By:- [Dataset]
. DOI: 10.5517/ccdc.csd.cc21dn37 HANDLE: 10754/664831
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. DOI: 10.5517/ccdc.csd.cc21dn15 HANDLE: 10754/664832
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. DOI: 10.5517/ccdc.csd.cc21dn26 HANDLE: 10754/664836
ae974a485f413a2113503eed53cd6c53
10.1021/jacs.9b10364