Synthesis 2017; 49(01): 87-95
DOI: 10.1055/s-0035-1561665
paper
© Georg Thieme Verlag Stuttgart · New York

Biology-Oriented Synthesis of 3,3-Spiro(2-tetrahydrofuranyl)oxindoles

Sandip Murarka
a   Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany   Email: andrey.antonchick@mpi-dortmund.mpg.de   Email: herbert.waldmann@mpi-dortmund.mpg.de
,
Christopher Golz
b   Inorganic Chemistry, Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
,
Carsten Strohmann
b   Inorganic Chemistry, Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
,
Andrey P. Antonchick*
a   Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany   Email: andrey.antonchick@mpi-dortmund.mpg.de   Email: herbert.waldmann@mpi-dortmund.mpg.de
c   Chemical Biology, Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 4a, 44227 Dortmund, Germany
,
Herbert Waldmann*
a   Department of Chemical Biology, Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany   Email: andrey.antonchick@mpi-dortmund.mpg.de   Email: herbert.waldmann@mpi-dortmund.mpg.de
c   Chemical Biology, Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 4a, 44227 Dortmund, Germany
› Author Affiliations
Further Information

Publication History

Received: 26 April 2016

Accepted after revision: 19 May 2016

Publication Date:
07 June 2016 (online)


Dedicated to Prof. Dieter Enders on the occasion of his 70th birthday

Abstract

A biology-oriented synthesis of 3,3-spiro(2-tetrahydrofuranyl)oxindole derivatives is realized through the rhodium(II)-catalyzed three-component reaction of diazoamides, aldehydes and β-nitrostyrenes. The reactions are conducted under mild conditions and the products are obtained in moderate to good yields with excellent regio- and diastereoselectivity.

Supporting Information