Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates
Pablo Barrio
1
,
Ignacio Ibáñez
2
,
LIDIA HERRERA
1
,
Raquel Román
1
,
Silvia Catalán
2
,
Santos Fustero
1, 2
Publication type: Journal Article
Publication date: 2015-06-29
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
26121312
General Chemistry
Catalysis
Organic Chemistry
Abstract
The asymmetric synthesis of fluorinated isoindolinones has been achieved by a palladium-catalyzed aminocarbonylation reaction of the corresponding α-fluoroalkyl o-iodobenzylamines. A base-mediated anti β-hydride elimination process was suggested to explain the partial erosion of the optical purity observed in some cases. This mechanistic rationale enabled the minimization of this partial racemization by fine-tuning the pKa of the base.
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36
Total citations:
36
Citations from 2025:
1
(2.78%)
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GOST
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Barrio P. et al. Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates // Chemistry - A European Journal. 2015. Vol. 21. No. 32. pp. 11579-11584.
GOST all authors (up to 50)
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Barrio P., Ibáñez I., HERRERA L., Román R., Catalán S., Fustero S. Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates // Chemistry - A European Journal. 2015. Vol. 21. No. 32. pp. 11579-11584.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/chem.201500773
UR - https://doi.org/10.1002/chem.201500773
TI - Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates
T2 - Chemistry - A European Journal
AU - Barrio, Pablo
AU - Ibáñez, Ignacio
AU - HERRERA, LIDIA
AU - Román, Raquel
AU - Catalán, Silvia
AU - Fustero, Santos
PY - 2015
DA - 2015/06/29
PB - Wiley
SP - 11579-11584
IS - 32
VL - 21
PMID - 26121312
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Barrio,
author = {Pablo Barrio and Ignacio Ibáñez and LIDIA HERRERA and Raquel Román and Silvia Catalán and Santos Fustero},
title = {Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates},
journal = {Chemistry - A European Journal},
year = {2015},
volume = {21},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/chem.201500773},
number = {32},
pages = {11579--11584},
doi = {10.1002/chem.201500773}
}
Cite this
MLA
Copy
Barrio, Pablo, et al. “Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium‐Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates.” Chemistry - A European Journal, vol. 21, no. 32, Jun. 2015, pp. 11579-11584. https://doi.org/10.1002/chem.201500773.