Angewandte Chemie International Edition
Explore this journal >
Communication

Exploration of Forbidden Povarov Processes as a Source of Unexpected Reactivity: A Multicomponent Mannich–Ritter Transformation†

Authors

  • Sara Preciado,

    1. Barcelona Science Park, Baldiri Reixac 10–12, 08028 Barcelona (Spain)
    Search for more papers by this author

  • Esther Vicente-García,

    1. Barcelona Science Park, Baldiri Reixac 10–12, 08028 Barcelona (Spain)
    Search for more papers by this author

  • Salomé Llabrés,

    1. Department of Physical Chemistry and Institute of Biomedicine (IBUB), Faculty of Pharmacy, University of Barcelona, Avda Diagonal 643, 08028 Barcelona (Spain)
    Search for more papers by this author

  • Prof. F. Javier Luque,

    1. Department of Physical Chemistry and Institute of Biomedicine (IBUB), Faculty of Pharmacy, University of Barcelona, Avda Diagonal 643, 08028 Barcelona (Spain)
    Search for more papers by this author

  • Prof. Rodolfo Lavilla

    Corresponding author
    1. Barcelona Science Park, Baldiri Reixac 10–12, 08028 Barcelona (Spain)
    2. Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Avda Joan XXIII s/n, 08028 Barcelona (Spain)
    • Barcelona Science Park, Baldiri Reixac 10–12, 08028 Barcelona (Spain)
    Search for more papers by this author
  • †

    This work was supported by DGICYT—Spain (projects BQUCTQ2009-07758 and SAF2011-27642), Generalitat de Catalunya (projects 2009SGR 1024 and 298), CESCA, and Grupo Ferrer (Barcelona, Spain).

Abstract

original image

When a door closes, a window opens! The use of geometrically or electronically restricted imines for Povarov-type processes does not afford the anti-Bredt tetrahydroquinolines, but leads instead to highly functionalized structures through novel reaction pathways (see picture; LA=Lewis acid). The exploration of “forbidden” routes constitutes a valuable approach in the search for new multicomponent reactions.

Continue reading full article

Ancillary

Article Information

DOI

10.1002/anie.201202927

Format Available

Full text: HTML | PDF

Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Request Permissions

Keywords

  • domino reactions;
  • heterocycles;
  • multicomponent reactions;
  • Ritter reaction;
  • Schiff bases

Publication History

  • Issue online:
  • Version of record online:
  • Manuscript Received:

Funded by

  • DGICYT—Spain. Grant Numbers: BQUCTQ2009-07758, SAF2011-27642
  • Generalitat de Catalunya. Grant Number: 2009SGR 1024 and 298
  • CESCA
  • Grupo Ferrer

Supporting Information

Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.

FilenameDescription
anie_201202927_sm_miscellaneous_information.pdf1275Kmiscellaneous_information

Please note: Wiley-Blackwell is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Related content

Articles related to the one you are viewing

Citing Literature

  • Number of times cited: 16
  1. 1Hui-Xin Luo, You-Hong Niu, Xiao-Ping Cao, Xin-Shan Ye, Cyclopropenes for the Synthesis of Cyclopropane-Fused Dihydroquinolines and Benzazepines, Advanced Synthesis & Catalysis, 2015, 357, 13, 2893Wiley Online Library
  2. 2Chepuri V. Suneel Kumar, Chepuri V. Ramana, Ru-Catalyzed Redox-Neutral Cleavage of the N–O Bond in Isoxazolidines: Isatogens to Pseudoindoxyls via a One-Pot [3 + 2]-Cycloaddition/N–O Cleavage, Organic Letters, 2015, 17, 12, 2870CrossRef
  3. 3Mahesh Kasthuri, Srinuvasu Nakka, H. Sharath Babu, Ch. Sudhakar, M. Venkatanarayana, P. V. Nagendra Kumar, BF3^|^middot;Et2O-catalyzed One-pot Synthesis of N,N^|^prime;-(2-Alkyl-1,3-diarylprop-1-ene-1,3-diyl)diacetamides through a Tandem Aldol^|^ndash;Double Ritter-type Reaction, Chemistry Letters, 2014, 43, 11, 1731CrossRef
  4. 4Julien Brioche, Thibaut Courant, Lilian Alcaraz, Michael Stocks, Mark Furber, Jieping Zhu, Géraldine Masson, Chiral Phosphoric Acid-Catalyzed Enantioselective Three- Component Aza-Diels-Alder Reactions of Aminopyrroles and Aminopyrazoles, Advanced Synthesis & Catalysis, 2014, 356, 8, 1719Wiley Online Library
  5. 5R. Bishop, Comprehensive Organic Synthesis II, 2014, 239CrossRef
  6. 6Pan-Lin Shao, Jia-Yu Liao, Yee Ann Ho, Yu Zhao, Highly Diastereo- and Enantioselective Silver-Catalyzed Double [3+2] Cyclization of α-Imino Esters with Isocyanoacetate, Angewandte Chemie, 2014, 126, 21, 5539Wiley Online Library
  7. 7Pan-Lin Shao, Jia-Yu Liao, Yee Ann Ho, Yu Zhao, Highly Diastereo- and Enantioselective Silver-Catalyzed Double [3+2] Cyclization of α-Imino Esters with Isocyanoacetate, Angewandte Chemie International Edition, 2014, 53, 21, 5435Wiley Online Library
  8. 8Esther Vicente-García, Nicola Kielland, Rodolfo Lavilla, Multicomponent Reactions in Organic Synthesis, 2014, 159CrossRef
  9. 9Guillaume Dagousset, William Erb, Jieping Zhu, Géraldine Masson, Phosphoric Acid Catalyzed Diastereo- and Enantioselective Synthesis of Substituted 1,3-Diaminotetralins, Organic Letters, 2014, 16, 9, 2554CrossRef
  10. 10Ala Bunescu, Qian Wang, Jieping Zhu, Three-Component Povarov Reaction–Heteroannulation with Arynes: Synthesis of 5,6-Dihydroindolo[1,2-a]quinolines, Organic Letters, 2014, 16, 6, 1756CrossRef
  11. 11Jing-Xin Liu, Qing-Qing Zhou, Jin-Gen Deng, Ying-Chun Chen, An asymmetric normal-electron-demand aza-Diels–Alder reaction via trienamine catalysis, Organic & Biomolecular Chemistry, 2013, 11, 47, 8175CrossRef
  12. 12John M. Knapp, Mark J. Kurth, Jared T. Shaw, Ashkaan Younai, Diversity-Oriented Synthesis, 2013, 27CrossRef
  13. 13Salomé Llabrés, Esther Vicente-García, Sara Preciado, Cristina Guiu, Ramon Pouplana, Rodolfo Lavilla, F. Javier Luque, Evolution of a Multicomponent System: Computational and Mechanistic Studies on the Chemo- and Stereoselectivity of a Divergent Process, Chemistry - A European Journal, 2013, 19, 40, 13355Wiley Online Library
  14. 14Arne Dieckmann, Matthew T. Richers, Alena Yu. Platonova, Chen Zhang, Daniel Seidel, K. N. Houk, Metal-Free α-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates, The Journal of Organic Chemistry, 2013, 78, 8, 4132CrossRef
  15. 15Justin M. Lopchuk, , 2013, 25, 137CrossRef
  16. 16Sara Preciado, Esther Vicente-Garcia, Salome Llabres, F. Javier Luque, Rodolfo Lavilla, ChemInform Abstract: Exploration of Forbidden Povarov Processes as a Source of Unexpected Reactivity: A Multicomponent Mannich-Ritter Transformation., ChemInform, 2012, 43, 52, noWiley Online Library