Rossi-Ashton, James A, Clarke, Aimee K, Donald, James R orcid.org/0000-0002-2176-4902 et al. (4 more authors) (2020) Iridium Catalyzed Enantioselective Intermolecular Indole C2-Allylation. Angewandte Chemie International Edition. pp. 7598-7604. ISSN 1433-7851
Abstract
The enantioselective intermolecular C2-allylation of 3-substituted indoles is reported for the first time. This directing group-free approach relies on a chiral Ir-(P, olefin) complex and Mg(ClO4)2 Lewis acid catalyst system to promote allylic substitution, providing the C2-allylated products in typically high yields (40-99%) and enantioselectivities (83-99% ee) with excellent regiocontrol. Experimental studies and DFT calculations suggest that the reaction proceeds via direct C2-allylation, rather than C3-allylation followed by in situ migration. Steric congestion at the indole-C3 position and improved π-π stacking interactions have been identified as major contributors to the C2-selectivity.
Metadata
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Copyright, Publisher and Additional Information: | © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details. | ||||
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Institution: | The University of York | ||||
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) | ||||
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Depositing User: | Pure (York) | ||||
Date Deposited: | 26 Feb 2020 09:10 | ||||
Last Modified: | 31 Jan 2024 00:58 | ||||
Published Version: | https://doi.org/10.1002/anie.202001956 | ||||
Status: | Published | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1002/anie.202001956 |
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