Vinyl boron ate complexes of enantioenriched secondary alkyl pinacolboronic esters undergo stereospecific radical-induced 1,2-migration in radical polar crossover reactions. In this three-component process various commercially available alkyl iodides act as radical precursors and light is used for chain initiation. Subsequent oxidation and protodeborylation leads to valuable α-chiral ketones and chiral alkanes, respectively, with excellent enantiopurity.
Keywords: boronic esters; protodeborylation; radical polar crossover reactions; α-chiral ketones.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.