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

Džambaski, Z., Tzaras, D.-I., Lee, S., Kokotos, C. G., & Bondzic, B. P. (2019). Enantioselective Organocatalytic Enamine C−H Oxidation/Diels‐ Alder Reaction. Advanced Synthesis & Catalysis, 361(8), 1792-1797. doi:10.1002/adsc.201900061.

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 Creators:
Džambaski, Zdravko1, Author
Tzaras, Dimitrios-Ioannis2, Author
Lee, Sunggi3, Author              
Kokotos, Christoforos G.2, Author
Bondzic, Bojan P.1, Author
Affiliations:
1Center for Chemistry, ICTM institute, University of Belgrade, Njegoseva 12, 11 000 Belgrade, Serbia, ou_persistent22              
2Laboratory of Organic Chemistry, Departmentof Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771 Athens, Greece, ou_persistent22              
3Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: Asymmetric catalysis; Cycloaddition; C-H oxidation; Diarylprolinols; Organocatalysis
 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.

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Language(s): eng - English
 Dates: 2019-01-142019-02-012019-04-16
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/adsc.201900061
 Degree: -

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Title: Advanced Synthesis & Catalysis
  Abbreviation : Adv. Synth. Catal.
Source Genre: Journal
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Publ. Info: Weinheim, Fed. Rep. of Germany : Wiley-VCH Verlag GmbH
Pages: - Volume / Issue: 361 (8) Sequence Number: - Start / End Page: 1792 - 1797 Identifier: ISSN: 1615-4150
CoNE: https://pure.mpg.de/cone/journals/resource/958634688013