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

12 June 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


Asymmetric reduction
Boronic Esters Efficient Syntheses
Main Group Elements


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