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Issue 23, 2015
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Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines

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Abstract

The uncatalysed cycloaddition of substituted diaryldiazo compounds onto bicyclic unsaturated lactams derived from pyroglutamic acid efficiently leads to highly functionalised azatricyclononanes. The products are readily elaborated to deprotected pyroglutamate derivatives, providing rapid access to conformationally constrained amino acids and their analogues. Preliminary assessment of antibacterial activity against one Gram positive and one Gram negative organism indicated high levels of efficacy in some cases.

Graphical abstract: Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines

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Publication details

The article was received on 01 Apr 2015, accepted on 05 May 2015 and first published on 05 May 2015


Article type: Paper
DOI: 10.1039/C5OB00648A
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Org. Biomol. Chem., 2015,13, 6522-6550

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    Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines

    L. Harris, M. Gilpin, A. L. Thompson, A. R. Cowley and M. G. Moloney, Org. Biomol. Chem., 2015, 13, 6522
    DOI: 10.1039/C5OB00648A

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