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A Boron-Oxygen Transborylation Strategy for the Asymmetric Reduction of Ketones

preprint
submitted on 11.06.2020, 14:25 and posted on 12.06.2020, 08:17 by Kieran Nicholson, Joanne Dunne, Peter DaBell, Alexander Beaton Garcia, Andrew D. Bage, Jamie H. Docherty, Thomas A. Hunt, Thomas Langer, Stephen P. Thomas
The asymmetric reduction of ketones with pinacolborane (HBpin) has been catalysed by an enantioenriched borane catalyst, formed in situ from 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) and β-pinene. While previously only used stoichiometrically, this borane has now been rendered catalytic using a new turnover mechanism, B-O transborylation. Thermodynamic and kinetic parameters of the key B-O/B-H transborylation showed this is a sub-class of σ-bond metathesis.

History

Email Address of Submitting Author

stephen.thomas@ed.ac.uk

Institution

University of Edinburgh

Country

United Kingdom

ORCID For Submitting Author

0000-0001-8614-2947

Declaration of Conflict of Interest

No conflict of interest

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