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Issue 12, 2015
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Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes

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Abstract

N-Heterocyclic carbene (NHC)-catalyzed formal [3 + 2] annulation of α,β-unsaturated aldehydes with N-substituted isatilidenes resulting in the diastereoselective synthesis of cyclopentanone-fused spirooxindoles is demonstrated. Mechanistically, the reaction proceeds via the generation of homoenolate equivalent intermediates from NHC and enals, which on interception with isatilidenes afford spiro-heterocyclic compounds bearing an all-carbon quaternary spiro-center in moderate to good yields and generally with high diastereoselectivity. Moreover, the functionalization of the spirooxindoles as well as the initial studies on the enantioselective version of this reaction are presented.

Graphical abstract: Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes

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Publication details

The article was received on 31 Jul 2015, accepted on 24 Sep 2015 and first published on 29 Sep 2015


Article type: Research Article
DOI: 10.1039/C5QO00242G
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Citation: Org. Chem. Front., 2015,2, 1584-1588

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    Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes

    A. Patra, A. Bhunia, S. R. Yetra, R. G. Gonnade and A. T. Biju, Org. Chem. Front., 2015, 2, 1584
    DOI: 10.1039/C5QO00242G

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