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2013 | 1 | 1 |

Article title

Trienamines: Their Key Role in Extended Organocatalysis
for Diels-Alder Reactions

Content

Title variants

Languages of publication

EN

Abstracts

EN
Activation via trienamine intermediates is a synthetically useful protocol for
performing asymmetric Diels-Alder reactions controlled by a remote chiral
catalyst (a secondary or primary amine). Key features underpinning this
concept are the conformation towards the trienamine formation and also
the use of highly electrophilic dienophiles. This cycloaddition reaction allows
the application of asymmetric organocatalysis at a remote position, and the
synthesis of complex molecules short synthetic sequences is possible.

Publisher

Year

Volume

1

Issue

1

Physical description

Dates

received
14 - 3 - 2013
online
31 - 5 - 2013
accepted
6 - 4 - 2013

Contributors

  • Departamento de Química Orgánica I,
    Facultad de Químicas, Universidad
    Complutense de Madrid
  • Departamento de Química Orgánica
    (Módulo 1), Facultad de Ciencias,
    Universidad Autónoma de Madrid
    Cantoblanco, 28049-Madrid
author
  • Departamento de Química Orgánica
    (Módulo 1), Facultad de Ciencias,
    Universidad Autónoma de Madrid
    Cantoblanco, 28049-Madrid

References

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  • Jia Z.-J., Jiang H., Li J.-L., Gschwend B., Li Q.-Z., Yin X.,Grouleff J., Chen Y.-C., Jørgensen K. A., Trienamines inAsymmetric Organocatalysis: Diels−Alder and TandemReactions, J. Am. Chem. Soc. 2011, 133, 5053-5061.
  • a) Lin H., Danishefsky S. J., Gelsemine: A Thought-Provoking Target for Total Synthesis, Angew. Chem.,Int. Ed. 2003, 42, 36–51. b) Galliford C. V., Scheidt K. A.,Pyrrolidinyl-Spirooxindole Natural Products as Inspirationsfor the Development of Potential Therapeutic Agents, Angew.Chem., Int. Ed. 2007, 46, 8748-8758. c) Rottmann M. et al.,Spiroindolones, a Potent Compound Class for the Treatmentof Malaria, Science 2010, 329, 1175-1180.
  • Jia Z.-J., Zhou Q., Zhou Q.-Q., Chen P.-Q., Chen Y.-C, exo-Selective Asymmetric Diels–Alder Reaction of 2,4-Dienalsand Nitroalkenes by Trienamine Catalysis, Angew. Chem.,Int. Ed. 2011, 50, 8638-8641.[WoS]
  • Jiang H., Gschwend B., Albrecht Ł., Hansen S. G., JørgensenK. A., Asymmetric Trienamine Catalysis for the Constructionof Structurally Rigid Cyclic α,α-Disubstituted Amino AcidDerivatives, Chem. Eur. J. 2011, 17, 9032-9036.[WoS]
  • Liu Y., Nappi M., Erceo E., Vera S., Melchiorre P., AsymmetricCatalysis of Diels–Alder Reactions with in Situ GeneratedHeterocyclic ortho-Quinodimethanes, J. Am. Chem. Soc.2011, 133, 15212-15218.
  • Liu Y., Nappi M., Escudero-Adán E. C., MelchiorreP., Multicatalytic Asymmetric Synthesis of ComplexTetrahydrocarbazoles via a Diels–Alder/Benzoin ReactionSequence, Org. Lett. 2012, 14, 1310-1313.
  • Xiong X.-F., Zhou Q., Gu J., Dong L., Liu T.-Y., Chen Y.-C.,Trienamine Catalysis with 2,4-Dienones: Development andApplication in Asymmetric Diels–Alder Reactions, Angew.Chem., Int. Ed. 2012, 51, 4401–4404.[WoS]
  • Halskov K. S., Johansen T. K., Davis R. L., SteurerM., Jensen F., Jørgensen K. A., Cross-trienamines inAsymmetric Organocatalysis, J. Am. Chem. Soc. 2012, 134,12943−12946.
  • Dieckmann A., Breugst M. K., Houk N., Zwitterions andUnobserved Intermediates in Organocatalytic Diels–AlderReactions of Linear and Cross-Conjugated Trienamines, J.Am. Chem. Soc. 2013, 135, 3237−3242.[WoS]
  • Albrecht L., Acosta F. C., Fraile A., Albrecht A.,Christensen J., Jørgensen K. A., Enantioselective H-Bond-Directing Approach for Trienamine-mediated Reactions inAsymmetric Synthesis, Angew. Chem., Int. Ed. 2012, 51,9088-9092.[WoS]
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  • Jiang H., Rodríguez-Escrich C., Johansen T. K., DavisR. L., Jørgensen K. A., Organocatalytic Activation of Polycyclic Aromatic Compounds for Asymmetric Diels–Alder Reactions, Angew. Chem., Int. Ed. 2012, 51, 10271-10274.[WoS]
  • Rodríguez-Escrich C., Davis R. L., Jiang H., Stiller J.,Johansen, T. K., Jørgensen K. A., Breaking Symmetrywith Symmetry: Bifacial Selectivity in the AsymmetricCycloaddition of Anthracene Derivatives, Chem. Eur. J. 2012,19, 2932-2936.
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Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_asorg-2013-0001
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