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Synlett 2018; 29(04): 497-502
DOI: 10.1055/s-0036-1590940
letter
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed One-Pot Borylation/Intramolecular Asymmetric Arylation on α-Ketiminoamides: Innovative Approach to Chiral 3-Amino-2-oxindoles

Carolina S. Marques  *
a   Centro de Química de Évora, University of Évora, Institute for Research and Advanced Training, CLAV, Rua Romão Ramalho 59, 7000 Évora, Portugal   eMail: carolsmarq@uevora.pt   eMail: ajb@dquim.uevora.pt
,
Simon E. Lawrence 
b   School of Chemistry, Analytical and Biological Chemistry Research Facility, Solid State Pharmaceutical Centre, University College Cork, Cork, Ireland
,
Anthony J. Burke  *
a   Centro de Química de Évora, University of Évora, Institute for Research and Advanced Training, CLAV, Rua Romão Ramalho 59, 7000 Évora, Portugal   eMail: carolsmarq@uevora.pt   eMail: ajb@dquim.uevora.pt
c   Department of Chemistry, School of Science and Technology, University of Évora, CLAV, Rua Romão Ramalho 59, 7000 Évora, Portugal
› InstitutsangabenWe are grateful for the award of a post-doctoral grant to C.S.M. (FRH/BPD/92394/2013) from the Fundação para a Ciência e a Tecnologia (FCT). The authors gratefully acknowledge Fundo Europeu de Desenvolvimento Regional (FEDER)-INALENTEJO for funding the program INMOLFARM – Molecular Innovation and Drug Discovery (ALENT-07-0224-FEDER-001743) and for financing the acquisition of the NMR equipment, project LADECA (ALENT-07-0262-FEDER-001878). S.E.L. thanks University College Cork 2013 Research Fund and Science Foundation Ireland under grant no. 05/PICA/B802/EC07.
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Publikationsverlauf

Received: 30. August 2017

Accepted after revision: 04. Oktober 2017

Publikationsdatum:
03. November 2017 (online)

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Abstract

3-Amino-2-oxindole derivatives are a common framework found in many natural products and medicinal compounds and thus their synthesis is of significant importance. We report for the first time a one-pot approach for the synthesis of these compounds, using a bory­lation/intramolecular asymmetric arylation sequence starting from ­ortho-bromo-α-ketimino amide derivatives. Pd(OAc)2 was used as the pre-catalyst along with (R)-BINAP as the chiral source. We successfully obtained a family of 3-phenyl-3-(aryl-amino)-indolin-2-one derivatives (11 in total) with excellent yields (up to 98%) and enantioselectivities of up to 76% ee. The reaction is versatile and tolerant of a wide range of functional groups.

Key words

oxindoles - intramolecular - bis(pinacolate)diboron - palladium - arylation - α-ketimines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590940.
  • Supporting Information
 

  • References and Notes


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