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Issue 25, 2015
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Gallium(III)- and calcium(II)-catalyzed Meyer–Schuster rearrangements followed by intramolecular aldol condensation or endo-Michael addition

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Abstract

The first gallium- and calcium-catalyzed Meyer–Schuster rearrangements are described. Under substrate control, the incipient conjugated ketones can be trapped intramolecularly by β-keto esters or amides to yield cyclic products after aldol condensation or endo-Michael addition. An interesting additive effect that promotes the latter tandem process with calcium has been found.

Graphical abstract: Gallium(III)- and calcium(II)-catalyzed Meyer–Schuster rearrangements followed by intramolecular aldol condensation or endo-Michael addition

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Publication details

The article was received on 28 Nov 2014, accepted on 07 Dec 2014 and first published on 08 Dec 2014


Article type: Communication
DOI: 10.1039/C4CC09514F
Citation: Chem. Commun., 2015,51, 5318-5321
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    Gallium(III)- and calcium(II)-catalyzed Meyer–Schuster rearrangements followed by intramolecular aldol condensation or endo-Michael addition

    M. Presset, B. Michelet, R. Guillot, C. Bour, S. Bezzenine-Lafollée and V. Gandon, Chem. Commun., 2015, 51, 5318
    DOI: 10.1039/C4CC09514F

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