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Issue 15, 2010
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A three-step tandem process for the synthesis of bicyclic γ-lactams

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Abstract

A one-pot, three-step tandem process has been developed for the direct synthesis of functionalised bicyclic [3.3.0], [4.3.0] and [5.3.0] γ-lactams from simple allylic trichloroacetimidates. The process involves a palladium(II) mediated Overman rearrangement followed by the use of Grubbs first generation complex which catalyzes both a ring closing metathesis reaction and a Kharasch cyclization. As well as exploring the scope of this process for the synthesis of a range of functionalised bicyclic γ-lactams, the use of chiral palladium(II) catalysts during the Overman rearrangement for the enantioselective synthesis of the bicyclic γ-lactams is also demonstrated.

Graphical abstract: A three-step tandem process for the synthesis of bicyclic γ-lactams

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Publication details

The article was received on 29 Mar 2010, accepted on 04 May 2010 and first published on 28 May 2010


Article type: Paper
DOI: 10.1039/C004695G
Citation: Org. Biomol. Chem., 2010,8, 3418-3425

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    A three-step tandem process for the synthesis of bicyclic γ-lactams

    F. I. McGonagle, L. Brown, A. Cooke and A. Sutherland, Org. Biomol. Chem., 2010, 8, 3418
    DOI: 10.1039/C004695G

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