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

ABSTRACT: 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 ?-chiral ketones and chiral alkanes, respectively, with excellent enantiopurity.

SUBMITTER: Gerleve C 

PROVIDER: S-EPMC5838550 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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

Gerleve Carolin C   Kischkewitz Marvin M   Studer Armido A  

Angewandte Chemie (International ed. in English) 20180116 9

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. ...[more]

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