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Issue 75, 2013
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Addition of lithium carbenoids to isocyanates: a direct access to synthetically useful N-substituted 2-haloacetamides

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Abstract

The addition of lithium carbenoids to isocyanates provides a versatile access to N-substituted 2-haloacetamides: the reaction tolerates the presence of variously functionalized substituents on the nitrogen atom, including sterically demanding ones and reactive halogens. No erosion of the enantiopurity was observed in the case of optically active isocyanates. One of the substrates prepared has been employed in Charette's type chemoselective addition of a Grignard reagent to access an α-chloroketone.

Graphical abstract: Addition of lithium carbenoids to isocyanates: a direct access to synthetically useful N-substituted 2-haloacetamides

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Publication details

The article was received on 06 Jun 2013, accepted on 09 Jul 2013 and first published on 09 Jul 2013


Article type: Communication
DOI: 10.1039/C3CC44255A
Citation: Chem. Commun., 2013,49, 8383-8385
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    Addition of lithium carbenoids to isocyanates: a direct access to synthetically useful N-substituted 2-haloacetamides

    V. Pace, L. Castoldi and W. Holzer, Chem. Commun., 2013, 49, 8383
    DOI: 10.1039/C3CC44255A

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