Ketone-Imide versus Ketone-Oxime Reductive Cross-Coupling Promoted by Samarium Diiodide:  New Mechanistic Insight Gained from a Failed Aminocyclopentitol Synthesis

10 páginas, 5 figuiras, 5 esquemas, 2 tablas.-- Supporting Information Available: General experimental procedures, 1D (1H and 13C) and 2D NMR (DQ-COSY, NOESY, HSQC, and HMBC) spectra for compounds 11-15, and energies and Cartesian coordinates for compounds in Table 2. This material is available free of charge via the Internet at http://pubs.acs.org.

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PID https://www.doi.org/10.1021/jo050185y
PID handle:10261/30950
PID https://www.doi.org/10.1021/jo050185y.s001
URL https://pubs.acs.org/doi/pdf/10.1021/jo050185y
URL https://pubs.acs.org/doi/10.1021/jo050185y
URL http://digital.csic.es/handle/10261/30950
URL http://hdl.handle.net/10261/30950
URL https://digital.csic.es/bitstream/10261/30950/1/jo050185y.pdf
URL https://academic.microsoft.com/#/detail/1977026202
URL https://core.ac.uk/display/36041303
URL http://digital.csic.es/bitstream/10261/30950/1/jo050185y.pdf
URL http://dx.doi.org/10.1021/jo050185y
URL https://figshare.com/articles/journal_contribution/Ketone_Imide_versus_Ketone_Oxime_Reductive_Cross_Coupling_Promoted_by_Samarium_Diiodide_New_Mechanistic_Insight_Gained_from_a_Failed_Aminocyclopentitol_Synthesis/3286513
URL http://europepmc.org/abstract/MED/15876107
URL https://www.ncbi.nlm.nih.gov/pubmed/15876107
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Access Right Open Access
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Author Jose Luis Chiara, 0000-0002-8153-1852
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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)
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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
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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)