Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 24, Pages 4176-4188Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600638
Keywords
Synthetic methods; Regioselectivity; Elimination; Protecting groups; Cyanoamides; Enamides
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Treatment of easily available ketone-derived cyanoamides with NaOtBu leads to enamides in a simple, scalable, and inexpensive one-step operation in good yield. Enamides not stabilized by conjugation or by inclusion in a ring can also be prepared. An E1cB mechanism consistent with all results and observations, is proposed. The Z geometry of the product enamide is highly favoured, and the regioselectivity can be directed by ones choice of protecting group.
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