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Synthesis of α‐Chiral Ketones and Chiral Alkanes Using Radical Polar Crossover Reactions of Vinyl Boron Ate Complexes
Author(s) -
Gerleve Carolin,
Kischkewitz Marvin,
Studer Armido
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711390
Subject(s) - stereospecificity , chemistry , alkyl , boron , polar , crossover , organic chemistry , polymer chemistry , medicinal chemistry , catalysis , physics , astronomy , artificial intelligence , computer science
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 α‐chiral ketones and chiral alkanes, respectively, with excellent enantiopurity.