Saruengkhanphasit, R., Collier, D. and Coldham, I. orcid.org/0000-0003-4602-6292 (2017) Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones. The Journal of Organic Chemistry, 82 (12). pp. 6489-6496. ISSN 0022-3263
Abstract
Aliphatic ketones containing a chloride and alkene were heated with hydroxylamine to promote cascade, tandem condensation to oximes, cyclization to nitrones, and 1,3-dipolar cycloaddition to tricyclic isoxazolidines as single stereoisomers. Single regioisomers were obtained when three atoms linked the ketone and dipolarophile to give five-membered rings but mixtures resulted with four atoms in the tether unless a terminal ester was located on the alkene. The N−O bond in the products could be reduced to give spirocyclic amines and diamines.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2017 American Chemical Society. This is an author produced version of a paper subsequently published in Journal of Organic Chemistry. Uploaded in accordance with the publisher's self-archiving policy. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 09 Jun 2017 11:27 |
Last Modified: | 01 Jun 2018 00:39 |
Published Version: | https://doi.org/10.1021/acs.joc.7b00959 |
Status: | Published |
Publisher: | American Chemical Society |
Refereed: | Yes |
Identification Number: | 10.1021/acs.joc.7b00959 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:117485 |