Practical syntheses of a series of novel ynamides and allenamides are described here.
While a base-induced isomerization protocol of propargyl amides leads to an array of chiral
and achiral allenamides, ynamides are prepared from enamides via bromination followed by
base-induced elimination of the Z-bromoenamides. These ynamides and allenamides
possess improved thermal stability compared to ynamines and allenamines. They can be
isolated, purified, and handled with ease, and thus, should be synthetically more useful than …