Synthesis 2020; 52(14): 2038-2044
DOI: 10.1055/s-0040-1707472
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed [3+2] Cycloaddition of Vinylaziridine and Indane-1,3-diones: Diastereo- and Enantioselective Access to Spiro-Pyrrolidines

Authors

  • Fabrizio Vetica

    a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: fabrizio.vetica@isof.cnr.it
  • Stephen J. Bailey

    a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: fabrizio.vetica@isof.cnr.it
  • Mukesh Kumar

    a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: fabrizio.vetica@isof.cnr.it
  • Suruchi Mahajan

    a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: fabrizio.vetica@isof.cnr.it
  • Carolina von Essen

    b   Department of Chemistry, Nanoscience Centre University of Jyvaskyla, 40014 JYU, Finland
  • Kari Rissanen

    b   Department of Chemistry, Nanoscience Centre University of Jyvaskyla, 40014 JYU, Finland
  • Dieter Enders

    a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   eMail: fabrizio.vetica@isof.cnr.it
Weitere Informationen

Publikationsverlauf

Received: 07. Januar 2020

Accepted after revision: 24. März 2020

Publikationsdatum:
07. April 2020 (online)


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§ These authors contributed equally to the work

Deceased

Abstract

A mild and efficient palladium-catalyzed [3+2] cycloaddition of vinylaziridine and indane-1,3-diones has been realized. The resulting spiro-pyrrolidines were provided in excellent yields and, with the introduction of the leucine-derived phosphine ligand, moderate to good enantio­- and diastereoselectivities.

Supporting Information