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Cinchona derivatives as sustainable and recyclable homogeneous organocatalysts for aza-Markovnikov addition

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Abstract

Three cinchona derivatives have shown remarkable activity to catalyze the aza-Markovnikov addition reaction of N-heterocycles to vinyl esters. The synthesis of aza-Markovnikov adducts possessing valuable biological activity was thoroughly optimized. By studying the ratio of the starting materials, bases and solvents, we achieved a new and efficient protocol, which could be performed under mild conditions with a small excess of vinyl ester affording products with excellent yields and high regioselectivity. This optimization reduced Sheldon's E-factor of the reaction by 42%. Furthermore, membrane separation for catalyst recycling was assessed to further improve the sustainability of the synthesis.

Graphical abstract: Cinchona derivatives as sustainable and recyclable homogeneous organocatalysts for aza-Markovnikov addition

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Publication details

The article was received on 15 Mar 2018, accepted on 12 Apr 2018 and first published on 12 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ01277F
Citation: New J. Chem., 2018, Advance Article
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    Cinchona derivatives as sustainable and recyclable homogeneous organocatalysts for aza-Markovnikov addition

    S. Nagy, Z. Fehér, P. Kisszékelyi, P. Huszthy and J. Kupai, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ01277F

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