Palladium‐Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ‐Lactams with Aryl Chlorides and Bromides

Herein, we report the first Pd‐catalyzed enantioselective arylation of α‐substituted γ‐lactams. Two sets of conditions were developed for this transformation, allowing for the use of either aryl chlorides or bromides as electrophiles. Utilizing a highly electron‐rich dialkylphosphine ligand we have...

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Bibliographic Details
Published in:Angewandte Chemie 2019-03, Vol.131 (13), p.4341-4345
Main Authors: Jette, Carina I., Geibel, Irina, Bachman, Shoshana, Hayashi, Masaki, Sakurai, Shunya, Shimizu, Hideki, Morgan, Jeremy B., Stoltz, Brian M.
Format: Article
Language:English
Subjects:
Aromatic compounds
Asymmetrische Katalyse
Bromides
Chemistry
Chlorides
Enantiomers
Palladium
Quartäre Stereozentren
Stickstoffheterocyclen
α-Arylierung
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Summary:Herein, we report the first Pd‐catalyzed enantioselective arylation of α‐substituted γ‐lactams. Two sets of conditions were developed for this transformation, allowing for the use of either aryl chlorides or bromides as electrophiles. Utilizing a highly electron‐rich dialkylphosphine ligand we have been able to construct α‐quaternary centers in good yields (up to 91 % yield) and high enantioselectivities (up to 97 % ee). Unter zwei Bedingungen: Für die erste Pd‐katalysierte enantioselektive Arylierung α‐substituierter γ‐Lactame wurden zwei Sätze von Reaktionsbedingungen entwickelt, was die Verwendung von entweder Arylchloriden oder ‐bromiden als Elektrophile ermöglichte. Beim Einsatz kommerziell verfügbarer Ferrocelan‐Liganden wurden quartäre Zentren in α‐Position in guten Ausbeuten (bis 91 %) und mit hohen Enantioselektivitäten (bis 97 % ee) aufgebaut.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201814475