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Silver-Assisted [3+2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones
Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synth Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synth Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China..
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.ORCID iD: 0000-0002-6089-5454
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2020 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 85, no 5, p. 3560-3567Article in journal (Refereed) Published
Abstract [en]

A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-S-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2020. Vol. 85, no 5, p. 3560-3567
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Biological Sciences
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URN: urn:nbn:se:kth:diva-271934DOI: 10.1021/acs.joc.9b03279ISI: 000518875700063PubMedID: 32013428Scopus ID: 2-s2.0-85080100235OAI: oai:DiVA.org:kth-271934DiVA, id: diva2:1424921
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QC 20200420

Available from: 2020-04-20 Created: 2020-04-20 Last updated: 2020-04-20Bibliographically approved

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Shatskiy, AndreyKärkäs, Markus D.

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