Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction
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2021
Authors
Džambaski, ZdravkoBondžić, Aleksandra M.
Triandafillidi, Ierasia
Kokotos, Christoforos G.
Bondžić, Bojan P.
Article (Published version)
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Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).
Keywords:
Cyclopropanation / C−H oxidation / Diarylprolinols / One-pot reaction. / OrganocatalysisSource:
Advanced Synthesis and Catalysis, 2021, 363, 16, 4002-4008Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-MESTD-inst-2020-200026)
- The State Scholarships Foundation (IKY) [MIS 5033021]
- HFRI [655]
DOI: 10.1002/adsc.202100630
ISSN: 1615-4150
WoS: 000667158900001
Scopus: 2-s2.0-8510894343
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VinčaTY - JOUR AU - Džambaski, Zdravko AU - Bondžić, Aleksandra M. AU - Triandafillidi, Ierasia AU - Kokotos, Christoforos G. AU - Bondžić, Bojan P. PY - 2021 UR - https://vinar.vin.bg.ac.rs/handle/123456789/9871 AB - Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.). T2 - Advanced Synthesis and Catalysis T1 - Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction VL - 363 IS - 16 SP - 4002 EP - 4008 DO - 10.1002/adsc.202100630 ER -
@article{ author = "Džambaski, Zdravko and Bondžić, Aleksandra M. and Triandafillidi, Ierasia and Kokotos, Christoforos G. and Bondžić, Bojan P.", year = "2021", abstract = "Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).", journal = "Advanced Synthesis and Catalysis", title = "Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction", volume = "363", number = "16", pages = "4002-4008", doi = "10.1002/adsc.202100630" }
Džambaski, Z., Bondžić, A. M., Triandafillidi, I., Kokotos, C. G.,& Bondžić, B. P.. (2021). Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction. in Advanced Synthesis and Catalysis, 363(16), 4002-4008. https://doi.org/10.1002/adsc.202100630
Džambaski Z, Bondžić AM, Triandafillidi I, Kokotos CG, Bondžić BP. Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction. in Advanced Synthesis and Catalysis. 2021;363(16):4002-4008. doi:10.1002/adsc.202100630 .
Džambaski, Zdravko, Bondžić, Aleksandra M., Triandafillidi, Ierasia, Kokotos, Christoforos G., Bondžić, Bojan P., "Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction" in Advanced Synthesis and Catalysis, 363, no. 16 (2021):4002-4008, https://doi.org/10.1002/adsc.202100630 . .