Alkayar, Z.T.I., Adams, H. and Coldham, I. (2016) Regiochemical and Stereochemical Studies of the Intramolecular Dipolar Cycloaddition of Nitrones Derived from Quaternary Aldehydes. SYNLETT, 27 (3). pp. 447-449. ISSN 0936-5214
Abstract
Three aldehydes each with a quaternary α-carbon stereocentre bearing an alkenyl, a phenyl, and a methyl ester group were treated with N-methylhydroxylamine. In each case bicyclic isoxazolidine products were formed by condensation to give intermediate nitrones that undergo intramolecular dipolar cycloaddition. The stereoselectivity was influenced by the α-carbonyl substituent, possibly by a hydrogen bond between CO and a nearby CH of the nitrone in the transition state (supported by DFT and X-ray studies), and the regioselectivity was affected by the length of the tether and by the presence of an ester on the alkene dipolarophile.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 Thieme Publishing. This is an author produced version of a paper subsequently published in SYNLETT. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | cycloaddition; diastereoselectivity; domino reaction; fused-ring systems; heterocycles |
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: | 04 Mar 2016 11:53 |
Last Modified: | 14 Apr 2017 15:46 |
Published Version: | https://dx.doi.org/10.1055/s-0035-1560906 |
Status: | Published |
Publisher: | Thieme Publishing |
Refereed: | Yes |
Identification Number: | 10.1055/s-0035-1560906 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:96025 |