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Issue 2, 2010
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Asymmetric 1,3-dipolar cycloadditions of acrylamides

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Abstract

This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references).

Graphical abstract: Asymmetric 1,3-dipolar cycloadditions of acrylamides

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Publication details

The article was received on 24 Jul 2009 and first published on 07 Dec 2009


Article type: Critical Review
DOI: 10.1039/B909358N
Citation: Chem. Soc. Rev., 2010,39, 845-883
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    Asymmetric 1,3-dipolar cycloadditions of acrylamides

    M. Kissane and A. R. Maguire, Chem. Soc. Rev., 2010, 39, 845
    DOI: 10.1039/B909358N

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