Synthesis
DOI: 10.1055/s-0036-1590918
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Cascade Synthesis of Tetrahydro­furanyl Spirooxindoles

Dmitri Trubitsõna, Sergei Žari, a, Sandra Kaabela, Marina Kudrjashovaa, Kadri Kriisa, Ivar Järvinga, Tõnis Pehkb, Tõnis Kanger*a
  • aDepartment of Chemistry and Biotechnology, School of Science, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
  • bNational Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
The authors thank the Estonian Ministry of Education and Research (grant nos. IUT19-32, IUT19-9, IUT23-7, PUT1468 and PUT692) and the Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013) for financial support.
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Publication History

Received: 20 July 2017

Accepted after revision: 05 September 2017

Publication Date:
18 September 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

An enantio- and regioselective organocatalytic cascade starting from isatin has been disclosed to construct tetrahydrofuranyl spirooxindoles in high yields and stereoselectivities. Also, a triple cascade leading to the pentacyclic compound with two quaternary and a tertiary stereocenter is described. The reactions were catalyzed by cinchonine-based thiourea.

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