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Synthesis and C-Alkylation of Hindered Aldehyde Enamines.

  作者 Hodgson, David M.;Bray, Christopher D.;Kindon, Nicholas D.;Reynolds, Nigel J.;Coote, Steven J.;Um, Joann M.;Houk, K. N.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2009年74-3;  页码  1019-1028  
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[摘要]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 examd. C- rather than N-alkylation was the dominant reaction pathway found with a range of electrophiles, making this route to a-alkylated aldehydes more synthetically useful than previously reported.

 
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