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Issue 1, 2012
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Rapid synthesis of highly functionalised α-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides

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Abstract

Four-component reactions between amino alcohols, aldehydes, isocyanides and thiols proceed rapidly under microwave or conventional heating at 60 °C in methanol. The reaction is successful with a wide range of components and gives access to potentially drug-like products containing amine, amide and thioether functionality in moderate to excellent yield. The reaction conditions are also applicable to the synthesis of a range of 8–10 membered medium ring lactonesvia three-component reactions of amino alcohols, isocyanides and acid-aldehydes. Incorporation of L-prolinol as the amino alcohol component in each case gives access to multicomponent products with moderate to high diastereoselectivity.

Graphical abstract: Rapid synthesis of highly functionalised α-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides

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Publication details

The article was received on 07 Sep 2011, accepted on 07 Oct 2011 and first published on 10 Oct 2011


Article type: Paper
DOI: 10.1039/C1OB06534C
Citation: Org. Biomol. Chem., 2012,10, 162-170
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    Rapid synthesis of highly functionalised α-amino amides and medium ring lactones using multicomponent reactions of amino alcohols and isocyanides

    M. Bachman, S. E. Mann and T. D. Sheppard, Org. Biomol. Chem., 2012, 10, 162
    DOI: 10.1039/C1OB06534C

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