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Inverse‐Electron‐Demand Palladium‐Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S‐Ligand and Hydrogen Bonding.
- Source :
- Angewandte Chemie International Edition; 8/5/2019, Vol. 58 Issue 32, p11013-11017, 5p
- Publication Year :
- 2019
-
Abstract
- Catalytic asymmetric cycloadditions of ambident Pd‐containing dipolar species with nucleophilic dipolarophiles, namely, inverse‐electron‐demand cycloadditions, are challenging and underdeveloped. Possibly, the inherent linear selectivity of Pd‐catalyzed intermolecular allylations and the lack of efficient chiral ligands are responsible for this limitation. Herein, two cycloadditions of such intermediates with deconjugated butenolides and azlactones were accomplished by using a novel chiral hybrid P,S‐ligand and hydrogen bonding. By doing so, highly functionalized, optically active dihydroquinol‐2‐ones were produced with generally high reaction efficiencies and selectivities. Preliminary DFT calculations were performed to explain the high enantio‐ and diastereoselectivities. [ABSTRACT FROM AUTHOR]
- Subjects :
- HYDROGEN bonding
PALLADIUM
RING formation (Chemistry)
ALLYLATION
BUTENOLIDES
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 58
- Issue :
- 32
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 137770678
- Full Text :
- https://doi.org/10.1002/anie.201905993