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Palladium-Catalyzed Enantioselective Arylation of Racemic Ketones to Form Bridged Bicycles via Dynamic Kinetic Resolution
- Source :
- Angewandte Chemie International Edition. 57:7673-7677
- Publication Year :
- 2018
- Publisher :
- Wiley, 2018.
-
Abstract
- Enantioselective α‐arylation of racemic ketones containing existing α′‐stereocenters is reported for the first time via base‐induced dynamic kinetic resolution. Bridged bicyclic rings are formed in good ee values, which are difficult to obtain otherwise. Furthermore, reactions in DMSO‐d6 resulted in extensive deuteration of both α‐ and α′‐positions in the products, thus supporting a pathway involving rapid, reversible deprotonation of ketones under catalytic conditions. MOE (Min. of Education, S’pore) Accepted version
- Subjects :
- chemistry.chemical_classification
Ketone
Alkylation
Bicyclic molecule
010405 organic chemistry
Chemistry
Enantioselective synthesis
chemistry.chemical_element
General Medicine
General Chemistry
010402 general chemistry
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
Stereocenter
Kinetic resolution
Palladium Catalysis
Deprotonation
Science::Chemistry [DRNTU]
Palladium
Subjects
Details
- ISSN :
- 14337851
- Volume :
- 57
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....4e3224470a1c9a9069d84a98be3d0b89
- Full Text :
- https://doi.org/10.1002/anie.201804318