Ketone-Imide versus Ketone-Oxime Reductive Cross-Coupling Promoted by Samarium Diiodide: New Mechanistic Insight Gained from a Failed Aminocyclopentitol Synthesis
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http://data.d4science.org/ctlg/RISIS2OpenData/dedup_wf_001--fe2fb5a1c0b91a2ed98e71c0f214539a |
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Identity
Access Modality
Field | Value |
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Access Right | Open Access |
Attribution
Field | Value |
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Author | Jose Luis Chiara, 0000-0002-8153-1852 |
Publishing
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Collected From | Digital.CSIC; ORCID; UnpayWall; figshare; Crossref; Microsoft Academic Graph |
Hosted By | Digital.CSIC; figshare; The Journal of Organic Chemistry |
Journal | The Journal of Organic Chemistry, 70, null |
Publication Date | 2016-05-06 |
Publisher | American Chemical Society (ACS) |
Additional Info
Field | Value |
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Country | Spain |
Description | The intramolecular 1,6-ketone/imide reductive coupling promoted by samarium diiodide competes favorably with an alternative 1,5-ketone/oxime ether coupling in a keto-oxime substrate derived from d-glucosamine N-protected with a phthalimido group. This pinacol coupling reaction affords new homochiral α-hydroxylactam scaffolds that could be useful in diversity-oriented synthesis. A mechanistic proposal for this reaction that explains the experimental results is supported by DFT quantum-mechanical calculations on model compounds. |
Description | Financial support by the Ministry of Science and Technology of Spain (project BQU2000-1501-C02-01) is gratefully acknowledged. |
Description | Peer reviewed |
Language | Undetermined |
Resource Type | Other literature type; Article |
system:type | publication |
Management Info
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Source | https://science-innovation-policy.openaire.eu/search/publication?articleId=dedup_wf_001::fe2fb5a1c0b91a2ed98e71c0f214539a |
Author | jsonws_user |
Last Updated | 24 December 2020, 21:24 (CET) |
Created | 24 December 2020, 21:24 (CET) |