Ravi, Saikiran Ravi, Fairlamb, Ian James Stewart orcid.org/0000-0002-7555-2761, Unsworth, William Paul orcid.org/0000-0002-9169-5156 et al. (1 more author) (2024) Asymmetric ‘Clip-Cycle’ synthesis of 3-spiropiperidines. Organic and Biomolecular Chemistry. ISSN 1477-0539
Abstract
3-Spiropiperidines can be synthesized in up to 87% yield and 96 : 4 er using a two step ‘Clip-Cycle’ approach. The ‘Clip’ stage of this method is based on efficient and highly E-selective cross metathesis of N-Cbz-protected 1-amino-hex-5-enes with a thioacrylate. This is followed by the ‘Cycle’ step, in which an intramolecular asymmetric aza-Michael cyclization is promoted by a chiral phosphoric acid catalyst.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | Publisher Copyright: © 2025 The Royal Society of Chemistry. |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number THE ROYAL SOCIETY INF\R2\202122 |
Depositing User: | Pure (York) |
Date Deposited: | 06 Dec 2024 12:40 |
Last Modified: | 06 Dec 2024 12:40 |
Published Version: | https://doi.org/10.1039/d4ob01608d |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1039/d4ob01608d |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:220559 |
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Description: Asymmetric ‘Clip-Cycle’ synthesis of 3-spiropiperidines†
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