Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.

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Abstract

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.
Original languageEnglish (US)
Pages (from-to)19415-19423
Number of pages9
JournalJournal of the American Chemical Society
Volume141
Issue number49
DOIs
StatePublished - Nov 8 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.

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