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Molecules 2018, 23(9), 2228; https://doi.org/10.3390/molecules23092228

Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones

Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China
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Received: 26 July 2018 / Revised: 26 August 2018 / Accepted: 29 August 2018 / Published: 1 September 2018
(This article belongs to the Special Issue Stereogenic Centers)
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Abstract

Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels–Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products. View Full-Text
Keywords: aza-Diels–Alder reaction; indoloquinolizidine-2-ones; enantioselective catalysis; cooperative catalysis; ruthenium aza-Diels–Alder reaction; indoloquinolizidine-2-ones; enantioselective catalysis; cooperative catalysis; ruthenium
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Wu, X.; Zhao, S.-B.; Zheng, L.-L.; Li, Y.-G. Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones. Molecules 2018, 23, 2228.

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