Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 32, Pages 11013-11017Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201905993
Keywords
cycloaddition; heterocycles; P; S ligand; hydrogen bonding; palladium
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Funding
- National Science Foundation of China [21822103, 21820102003, 21822303, 21772052, 21772053, 21572074 and 21472057] Funding Source: Medline
- Natural Science Foundation of Hubei Province [2017AHB047] Funding Source: Medline
- the Program of Introducing Talents of Discipline to Universities of China (111 Program) [B17019] Funding Source: Medline
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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.
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