Chambers, Sarah J, Coulthard, Graeme, Unsworth, William Paul orcid.org/0000-0002-9169-5156 et al. (2 more authors) (2016) From Heteroaromatic acids and Imines to Azaspirocycles:Stereoselective Synthesis and 3D Shape Analysis. Chemistry : A European Journal (Weinheim an der Bergstrasse, Germany). pp. 6496-6500. ISSN 1521-3765
Abstract
Heteroaromatic carboxylic acids have been directly coupled with imines using T3P and NEt(i-Pr)2 to form azaspirocycles via intermediate N-acyliminium ions. Spirocyclic indolenines (3H-indoles), azaindolenines, 2H-pyrroles and 3H-pyrroles were all accessed using this metal-free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under-represented in existing drugs and high throughput screening libraries.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 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. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 07 Mar 2016 11:46 |
Last Modified: | 16 Oct 2024 12:50 |
Published Version: | https://doi.org/10.1002/chem.201600823 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/chem.201600823 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:96114 |
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