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Issue 15, 2017
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An environmentally benign double Michael addition reaction of heterocyclic ketene aminals with quinone monoketals for diastereoselective synthesis of highly functionalized morphan derivatives in water

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Abstract

A efficient and concise one-pot procedure has been developed for the synthesis of highly functional morphan derivatives 3 based on diastereoselective double Michael addition reactions of various quinone monoketals 1 with a variety of heterocyclic ketene aminals (HKAs) 2 in the green solvent water at 60 °C. This protocol is especially suitable for efficient and rapid parallel syntheses of N-containing bridged heterocycles possessing pharmacological activities. As a result, a library of highly functional morphan derivatives was easily synthesized using this reported environmentally benign, mild, and catalyst-free one-pot reaction.

Graphical abstract: An environmentally benign double Michael addition reaction of heterocyclic ketene aminals with quinone monoketals for diastereoselective synthesis of highly functionalized morphan derivatives in water

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Publication details

The article was received on 17 May 2017, accepted on 20 Jun 2017 and first published on 20 Jun 2017


Article type: Paper
DOI: 10.1039/C7GC01435J
Citation: Green Chem., 2017,19, 3574-3584
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    An environmentally benign double Michael addition reaction of heterocyclic ketene aminals with quinone monoketals for diastereoselective synthesis of highly functionalized morphan derivatives in water

    Y. Ma, K. Wang, R. Huang, J. Lin and S. Yan, Green Chem., 2017, 19, 3574
    DOI: 10.1039/C7GC01435J

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