Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction
Authors
Džambaski, Zdravko
Tzaras, Dimitrios‐Ioannis
Lee, Sunggi
Kokotos, Christoforos G.
Bondžić, Bojan

Article (Accepted Version)
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α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.
Keywords:
Asymmetric catalysis / Cycloaddition / C−H oxidation / Diarylprolinols / OrganocatalysisSource:
Advanced Synthesis & Catalysis, 2019, 361, 8, 1792-1797Publisher:
- Wiley
Funding / projects:
- COST action CA15106: CH activation in organic synthesis (CHAOS)
- Special Account for Research Grants of the National and Kapodistrian University of Athens
- Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)
Note:
- This is peer-reviewed version of the article: Zdravko Dzambaski, Dimitrios Ioannis Tzaras, Sunggi Lee, Christoforos Kokotos, and Bojan Bondzic, Advanced Synthesis & Catalysis, 2019, 361, 8, 1792-1797, http://dx.doi.org/10.1002/adsc.201900061
- http://cer.ihtm.bg.ac.rs/handle/123456789/2953
DOI: 10.1002/adsc.201900061
ISSN: 1615-4150; 1615-4169
WoS: 000467075800011
Scopus: 2-s2.0-85061776252
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IHTMTY - JOUR AU - Džambaski, Zdravko AU - Tzaras, Dimitrios‐Ioannis AU - Lee, Sunggi AU - Kokotos, Christoforos G. AU - Bondžić, Bojan PY - 2019 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2954 AB - α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks. PB - Wiley T2 - Advanced Synthesis & Catalysis T1 - Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction VL - 361 IS - 8 SP - 1792 EP - 1797 DO - 10.1002/adsc.201900061 ER -
@article{ author = "Džambaski, Zdravko and Tzaras, Dimitrios‐Ioannis and Lee, Sunggi and Kokotos, Christoforos G. and Bondžić, Bojan", year = "2019", abstract = "α,β‐unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single‐electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels‐Alder reaction. This enantioselective one‐pot transformation represents the first example of saturated aldehydes being used in domino Diels‐Alder reaction processes and demonstrates the power of this protocol for construction of stereo‐defined chiral compounds and building blocks.", publisher = "Wiley", journal = "Advanced Synthesis & Catalysis", title = "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction", volume = "361", number = "8", pages = "1792-1797", doi = "10.1002/adsc.201900061" }
Džambaski, Z., Tzaras, D., Lee, S., Kokotos, C. G.,& Bondžić, B.. (2019). Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis Wiley., 361(8), 1792-1797. https://doi.org/10.1002/adsc.201900061
Džambaski Z, Tzaras D, Lee S, Kokotos CG, Bondžić B. Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. in Advanced Synthesis & Catalysis. 2019;361(8):1792-1797. doi:10.1002/adsc.201900061 .
Džambaski, Zdravko, Tzaras, Dimitrios‐Ioannis, Lee, Sunggi, Kokotos, Christoforos G., Bondžić, Bojan, "Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction" in Advanced Synthesis & Catalysis, 361, no. 8 (2019):1792-1797, https://doi.org/10.1002/adsc.201900061 . .