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Issue 49, 2019
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Lewis acid catalyzed annulation of spirocyclic donor–acceptor cyclopropanes with exo-heterocyclic olefins: access to highly functionalized bis-spirocyclopentane oxindole frameworks

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Abstract

Lewis acid catalyzed highly efficient [3+2] annulation of spirocyclic Donor–Acceptor cyclopropanes (DACs) with exo-heterocyclic olefins is reported to furnish various biologically relevant dispiro-2,3-dioxopyrrolidine[cyclopentane]oxindole and dispiropyrazolone[cyclopentane]oxindole frameworks. This report highlights the use of oxindole-activated spiro-DACs as potential synthons to access complex dispirocarbocyclic oxindoles via ring-enlargement of the former, with high yields and diastereoselectivity.

Graphical abstract: Lewis acid catalyzed annulation of spirocyclic donor–acceptor cyclopropanes with exo-heterocyclic olefins: access to highly functionalized bis-spirocyclopentane oxindole frameworks

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Article information


Submitted
02 May 2019
Accepted
24 May 2019
First published
24 May 2019

Chem. Commun., 2019,55, 7069-7072
Article type
Communication

Lewis acid catalyzed annulation of spirocyclic donor–acceptor cyclopropanes with exo-heterocyclic olefins: access to highly functionalized bis-spirocyclopentane oxindole frameworks

K. Singh, S. Pramanik, T. A. Hamlin, B. Mondal, D. Das and J. Saha, Chem. Commun., 2019, 55, 7069
DOI: 10.1039/C9CC03393A

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