4.8 Article

Synthesis of alpha-Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 9, Pages 2441-2444

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711390

Keywords

alpha-chiral ketones; boronic esters; protodeborylation; radical polar crossover reactions

Funding

  1. European Research Council ERC [692640]
  2. Fonds der Chemischen Industrie

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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 alpha-chiral ketones and chiral alkanes, respectively, with excellent enantiopurity.

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