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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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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cited_by cdi_FETCH-LOGICAL-c2025-d17c87991533fa19bae70a97316a4bf74634c2b4f9996e943bfc2665f86104fb3
cites cdi_FETCH-LOGICAL-c2025-d17c87991533fa19bae70a97316a4bf74634c2b4f9996e943bfc2665f86104fb3
container_end_page 4345
container_issue 13
container_start_page 4341
container_title Angewandte Chemie
container_volume 131
creator Jette, Carina I.
Geibel, Irina
Bachman, Shoshana
Hayashi, Masaki
Sakurai, Shunya
Shimizu, Hideki
Morgan, Jeremy B.
Stoltz, Brian M.
description 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.
doi_str_mv 10.1002/ange.201814475
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source Wiley-Blackwell Read & Publish Collection
subjects Aromatic compounds
Asymmetrische Katalyse
Bromides
Chemistry
Chlorides
Enantiomers
Palladium
Quartäre Stereozentren
Stickstoffheterocyclen
α-Arylierung
title Palladium‐Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ‐Lactams with Aryl Chlorides and Bromides
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