Revisiting the Baddeley Reaction: Access to Functionalized Decalins by Charge-Promoted Alkane Functionalization
- Author(s)
- Milos Vavrik, Phillip S. Grant, Daniel Kaiser, Tim Gruene, Nuno Maulide
- 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.
- Organisation(s)
- Department of Organic Chemistry, Core Facility Crystal Structure Analysis, Department of Inorganic Chemistry
- Journal
- Angewandte Chemie - International Edition
- Volume
- 64
- ISSN
- 1433-7851
- DOI
- https://doi.org/10.1002/anie.202418067
- Publication date
- 2024
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 104015 Organic chemistry
- Keywords
- ASJC Scopus subject areas
- Catalysis, General Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/f3de61b5-49bb-4ff5-bbab-e55db2138f40