Design of an organocatalyst for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins.

@article{Ishihara2005DesignOA,
  title={Design of an organocatalyst for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins.},
  author={K. Ishihara and K. Nakano},
  journal={Journal of the American Chemical Society},
  year={2005},
  volume={127 30},
  pages={
          10504-5
        }
}
  • K. Ishihara, K. Nakano
  • Published 2005
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • We have realized the first enantioselective organocatalytic Diels-Alder reaction between alpha-substituted acroleins, such as alpha-acyloxyacroleins, and not only cyclic but also acyclic dienes. alpha-Acyloxyacroleins are useful as synthetic equivalents of alpha-haloacroleins. The present catalyst could be prepared in situ from pentafluorobenzenesulfonic acid (2.5-3.0 equiv) and chiral triamine (1 equiv) derived from H-l-Phe-l-Leu-N(CH2CH2)2. The enantioselective Diels-Alder reaction of 5… CONTINUE READING
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