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  • Title: Synthesis and C-alkylation of hindered aldehyde enamines.
    Author: Hodgson DM, Bray CD, Kindon ND, Reynolds NJ, Coote SJ, Um JM, Houk KN.
    Journal: J Org Chem; 2009 Feb 06; 74(3):1019-28. PubMed ID: 19105636.
    Abstract:
    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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