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Issue 10, 2013
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A simple and highly effective water-compatible organocatalytic system for asymmetric direct Michael reactions of linear aldehydes to maleimides

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Abstract

Diarylprolinol silyl ether-based organocatalyst 2, in conjunction with ionic liquid supported (ILS) sulfonic acid 6a as co-catalyst, leads to a novel organocatalyst in aqueous media. The in situ generated catalyst demonstrated high reactivity and stereoselectivity for the Michael reactions of linear aldehydes to maleimides in brine without any organic solvents. For these reactions, up to 76% yield, 9 : 1 dr and 96% ee were obtained for a broad variety of aldehydes and maleimides.

Graphical abstract: A simple and highly effective water-compatible organocatalytic system for asymmetric direct Michael reactions of linear aldehydes to maleimides

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Publication details

The article was received on 30 May 2013, accepted on 02 Aug 2013 and first published on 06 Aug 2013


Article type: Communication
DOI: 10.1039/C3GC41024B
Citation: Green Chem., 2013,15, 2690-2694
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    A simple and highly effective water-compatible organocatalytic system for asymmetric direct Michael reactions of linear aldehydes to maleimides

    Y. Qiao and A. D. Headley, Green Chem., 2013, 15, 2690
    DOI: 10.1039/C3GC41024B

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