Lawer, Aggie, Rossi-Ashton, James A, Stephens, Thomas C et al. (4 more authors) (2019) Internal nucleophilic catalyst mediated cyclisation/ring expansion cascades for the synthesis of medium-sized lactones and lactams. Angewandte Chemie International Edition. pp. 13942-13947. ISSN 1433-7851
Abstract
A strategy for the synthesis of medium-sized lactones and lactams from linear precursors is described in which an amine acts as an internal nucleophilic catalyst to facilitate a novel cyclisation/ring expansion cascade sequence. This method obviates the need to use high-dilution conditions usually associated with medium-ring cyclisation protocols, as the reactions operate exclusively via kinetically favourable 'normal' sized cyclic transition states. This same feature also enables biaryl-containing medium-sized rings to be prepared with complete atroposelectivity via point-to-axial chirality transfer.
Metadata
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Copyright, Publisher and Additional Information: | © 2019 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. | ||||
Keywords: | atropisomers, axial chirality, medium-sized rings, pyridines, ring expansion | ||||
Dates: |
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Institution: | The University of York | ||||
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) | ||||
Funding Information: |
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Depositing User: | Pure (York) | ||||
Date Deposited: | 31 Jul 2019 10:40 | ||||
Last Modified: | 06 Dec 2023 13:14 | ||||
Published Version: | https://doi.org/10.1002/anie.201907206 | ||||
Status: | Published | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1002/anie.201907206 | ||||
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Filename: Aggie_NICE_paper_version_26_revision.docx
Description: Aggie NICE paper version 26 revision