Synthesis and C-alkylation of hindered aldehyde enamines.

Synthesis and C-alkylation of hindered aldehyde enamines.

A new reactivity mode of hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl hal...

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Detalles Bibliográficos
Autores principales: Hodgson, D, Bray, C, Kindon, N, Reynolds, N, Coote, S, Um, J, Houk, K
Formato: Journal article
Lenguaje:English
Publicado: 2009
Descripción
Sumario:A new reactivity mode of hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl halides. For comparison, the reactivity of aldehyde enamines synthesized via a traditional condensation method was examined. C- rather than N-alkylation was the dominant reaction pathway found with a range of electrophiles, making this route to alpha-alkylated aldehydes more synthetically useful than previously reported.

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