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Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction

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2019
10.1002_adsc.201900061.pdf (1.871Mb)
Authors
Džambaski, Zdravko
Tzaras, Dimitrios‐Ioannis
Lee, Sunggi
Kokotos, Christoforos G.
Bondžić, Bojan
Article (Accepted Version)
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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.
Keywords:
Asymmetric catalysis / Cycloaddition / C−H oxidation / Diarylprolinols / Organocatalysis
Source:
Advanced Synthesis & Catalysis, 2019, 361, 8, 1792-1797
Publisher:
  • 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
[ Google Scholar ]
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2954
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - 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 . .

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