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

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 additi...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-03, Vol.51 (25), p.5318-5321
Main Authors: Presset, M, Michelet, B, Guillot, R, Bour, C, Bezzenine-Lafollée, S, Gandon, V
Format: Article
Language:English
Subjects:
Additives
Aldehydes
Amides
Calcium
Chemical Sciences
Condensates
Esters
Ketones
Substrates
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc09514f