Titel
Revisiting the Baddeley Reaction: Access to Functionalized Decalins by Charge‐Promoted Alkane Functionalization
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Abstract
C−H functionalization of purely aliphatic substrates is a challenging endeavor, as the absence of directing groups generally thwarts attempts at regiocontrol. This is particularly true for difunctionalization reactions, where the control of relative stereochemistry poses an additional obstacle. The Baddeley reaction of decalins, despite suffering from strong limitations with regard to yield and generality, stands as one of only few known transformations capable of regio- and stereocontrol in aliphatic C−H functionalization. Herein, we report a regio- and diastereoselective method for the double functionalization of decalins enabling access to a novel, unreported regioisomer in synthetically useful yields. This method was also successfully applied to a range of other alkane substrates, enabling a straightforward synthesis of keto alcohols from the simplest alkane building blocks.
Stichwort
Baddeley reactiondecalinalkane functionalizationacylium ionoctalin
Objekt-Typ
Sprache
Englisch [eng]
Persistent identifier
phaidra.univie.ac.at/o:2120701
Erschienen in
Titel
Angewandte Chemie International Edition
Band
64
Ausgabe
5
ISSN
1433-7851
Erscheinungsdatum
2024
Publication
Wiley
Fördergeber
Europäische Union (alle Programme) — 682002
Erscheinungsdatum
2024
Zugänglichkeit
Rechte
Rechteangabe
© 2024 The Author(s)
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