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Synthesis and C-alkylation of hindered aldehyde enamines.

Authors
  • Hodgson, David M
  • Bray, Christopher D
  • Kindon, Nicholas D
  • Reynolds, Nigel J
  • Coote, Steven J
  • Um, Joann M
  • Houk, K N
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Feb 06, 2009
Volume
74
Issue
3
Pages
1019–1028
Identifiers
DOI: 10.1021/jo802016t
PMID: 19105636
Source
Medline
License
Unknown

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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