Synthesis and C-alkylation of hindered aldehyde enamines

…, NJ Reynolds, SJ Coote, JM Um, KN Houk

Index: Hodgson, David M.; Bray, Christopher D.; Kindon, Nicholas D.; Reynolds, Nigel J.; Coote, Steven J.; Um, Joann M.; Houk Journal of Organic Chemistry, 2009 , vol. 74, # 3 p. 1019 - 1028

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Citation Number: 24

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 ...