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

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
› Author Affiliations
Further Information

Publication History

Received: 07 January 2020

Accepted after revision: 24 March 2020

Publication Date:
07 April 2020 (online)


§ 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

 
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  • 3 Current address: Dr. M. Kumar, Department of Chemistry, Sahu Jain (P. G.) College, Najibabad 246763, Bijnor, Uttar Pradesh, India.
  • 4 Current address: Dr. S. Mahajan, Indian Institute of Technology Jammu, Jagti, NH-44, Nagrota, Jammu 181221, J & K, India.
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