Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 3, Pages 1019-1028Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802016t
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Funding
- EPSRC [GR/S46789/01]
- AstraZeneca for an Industrial CASE award
- Wadham College for a Keeley Senior Scholarship
- Glaxo-Smith-Kline for a CASE award
- National Institutes of General Medical Sciences, National Institutes of Health [G36700]
- National Mass Spectrometry Service Centre for mass spectra.
- Engineering and Physical Sciences Research Council [GR/S46789/01] Funding Source: researchfish
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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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