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