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Acid-Catalyzed In Situ Generation of Less Accessible or Unprecedented N-Boc Imines from N-Boc Aminals


  • This work was supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Advanced Molecular Transformations by Organocatalysts” from MEXT (Japan). T.Y. thanks the Japan Society for the Promotion of Science for Young Scientists for Research Fellowships.


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Crafty aminals: The in situ generation of hitherto unattainable alkynyl-substituted N-Boc-protected imines was realized by the acid-catalyzed elimination of tert-butyl carbamate from N-Boc aminals. A wide variety of N-Boc imines can be generated, which can then be utilized for subsequent carbon–carbon bond-forming reactions, such as Mannich-type reactions.