Synthesis 2017; 49(22): 4986-4995
DOI: 10.1055/s-0036-1590823
paper
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Synthesis of 2,3′-Connected Bis-Indolinones by Mannich Reactions of N-Acetylindolin-3-ones with Isatin N-Boc Ketimines

V. Pratap Reddy Gajulapallia, Ehsan Jafaria, Dipti S. Kundua, Suruchi Mahajana, Anssi Peuronenb, Kari Rissanenb, Dieter Enders*a
  • aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
  • bDepartment of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland   Email: enders@rwth-aachen.de
Further Information

Publication History

Received: 02 June 2017

Accepted: 06 June 2017

Publication Date:
01 August 2017 (eFirst)

Abstract

A highly diastereo- and enantioselective Mannich reaction of N-acetylindolin-3-ones with isatin N-Boc ketimines to form 2,3′-connected bis-indolinones is developed employing a low loading of a readily available bifunctional thiourea catalyst. The asymmetric synthesis connects two indolinones via a vic-diamine unit and generates two neighboring stereocenters.

Supporting Information

 
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