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Issue 3, 2011
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The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates

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Abstract

Introduction of a β-electron withdrawing group to cycloalkanones allows facile C–C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.

Graphical abstract: The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates

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Article information


Submitted
27 Aug 2010
Accepted
12 Oct 2010
First published
22 Nov 2010

Org. Biomol. Chem., 2011,9, 783-792
Article type
Paper

The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates

J. Hierold, T. Hsia and D. W. Lupton, Org. Biomol. Chem., 2011, 9, 783
DOI: 10.1039/C0OB00632G

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