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Molecules. 2018 Sep 1;23(9). pii: E2228. doi: 10.3390/molecules23092228.

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

Author information

1
Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China. wuxiang@hfut.edu.cn.
2
Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China. zsbhfut@mail.hfut.edu.cn.
3
Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China. zhengll@mail.hfut.edu.cn.
4
Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China. liyg@hfut.edu.cn.

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.

KEYWORDS:

aza-Diels–Alder reaction; cooperative catalysis; enantioselective catalysis; indoloquinolizidine-2-ones; ruthenium

PMID:
30200483
PMCID:
PMC6225203
DOI:
10.3390/molecules23092228
[Indexed for MEDLINE]
Free PMC Article

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