Transfer of 1‑Alkenyl Groups between Secondary Amines. Relative Stability and Reactivity of Enamines from Popular Organocatalysts

Transfer of 1‑Alkenyl Groups between Secondary Amines. Relative Stability and Reactivity of Enamines from Popular Organocatalysts

Enamines from 3-methylbutanal and several Pro- and Phe-derived secondary amines were prepared in DMSO-d 6, CD3CN, and CDCl3. For the first time, the relative thermodynamic stabilities of these and other enamines were compared, and rapid exchanges of 1-alkenyl groups were demonstrated. Competition ex...

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Veröffentlicht in:Organic letters 2014-06, Vol.16 (11), p.2900-2903
Hauptverfasser: Carneros, Héctor, Sánchez, Dani, Vilarrasa, Jaume
Format: Artikel
Sprache:eng
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Zusammenfassung:Enamines from 3-methylbutanal and several Pro- and Phe-derived secondary amines were prepared in DMSO-d 6, CD3CN, and CDCl3. For the first time, the relative thermodynamic stabilities of these and other enamines were compared, and rapid exchanges of 1-alkenyl groups were demonstrated. Competition experiments showed that the most favored enamines (without significant steric inhibition of resonance) react more rapidly with electrophiles.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501044u