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Issue 15, 2001
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Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

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Abstract

The aldehyde 2-formyl-2-(pent-4-enyl)-1,3-dithiane 1, containing both alkene and aldehyde functional groups, is a good substrate for intramolecular dipolar cycloaddition reactions after condensation with various N-alkyl α-amino-esters. This paper reports the optimization, scope and stereoselectivity of this reaction to give octahydroindoles (2-azabicyclo[4.3.0]nonanes).

Graphical abstract: Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

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Publication details

The article was received on 18 May 2001, accepted on 21 Jun 2001 and first published on 10 Jul 2001


Article type: Paper
DOI: 10.1039/B104390K
Citation: J. Chem. Soc., Perkin Trans. 1, 2001,0, 1758-1763
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    Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

    I. Coldham, K. M. Crapnell, J. D. Moseley and R. Rabot, J. Chem. Soc., Perkin Trans. 1, 2001, 0, 1758
    DOI: 10.1039/B104390K

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