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Synthesis 2017; 49(22): 4986-4995
DOI: 10.1055/s-0036-1590823
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© 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 Gajulapalli
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Ehsan Jafari
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Dipti S. Kundu
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Suruchi Mahajan
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Anssi Peuronen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland   Email: enders@rwth-aachen.de
,
Kari Rissanen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland   Email: enders@rwth-aachen.de
,
Dieter Enders*
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
› Author Affiliations
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Publication History

Received: 02 June 2017

Accepted: 06 June 2017

Publication Date:
01 August 2017 (online)

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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.

Key words

asymmetric synthesis - indolinone - bifunctional thiourea - organocatalysis - Mannich reaction

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    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590823 .
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