Oxonitriles: a grignard addition-acylation route to enamides.

@article{Fleming2006OxonitrilesAG,
  title={Oxonitriles: a grignard addition-acylation route to enamides.},
  author={Fraser F Fleming and Guoqing Wei and Zhiyu Zhang and Omar W. Steward},
  journal={Organic letters},
  year={2006},
  volume={8 21},
  pages={4903-6}
}
[reaction: see text] Sequential addition of three different Grignard reagents and pivaloyl chloride to 3-oxo-1-cyclohexene-1-carbonitrile installs four new bonds to generate a diverse array of cyclic enamides. Remarkably, formation of the C-magnesiated nitrile intermediate is followed by preferential acylation by pivaloyl chloride rather than consumption by an in situ Grignard reagent. Rapid N-acylation of the C-magnesiated nitrile generates an acyl ketenimine that reacts readily with Grignard… CONTINUE READING