Chiral Pyridinium Phosphoramide as a Dual Brønsted Acid Catalyst for Enantioselective Diels-Alder Reaction.

@article{Nishikawa2016ChiralPP,
  title={Chiral Pyridinium Phosphoramide as a Dual Br{\o}nsted Acid Catalyst for Enantioselective Diels-Alder Reaction.},
  author={Yasuhiro Nishikawa and Saki Nakano and Yuu Tahira and Kanako Terazawa and Ken Yamazaki and Chitoshi Kitamura and Osamu Hara},
  journal={Organic letters},
  year={2016},
  volume={18 9},
  pages={
          2004-7
        }
}
Chiral pyridinium phosphoramide 1·HX was designed to be a new class of chiral Brønsted acid catalyst in which both the pyridinium proton and the adjacent imide-like proton activated by the electron-withdrawing pyridinium moiety could work cooperatively as strong dual proton donors. The potential of 1·HX was shown in the enantioselective Diels-Alder reactions of 1-amino dienes with various dienophiles including N-unsubstituted maleimide, which has yet to be successfully used in an asymmetric… CONTINUE READING
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