Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides

Michael J. Di Maso, Kevin M. Snyder, Fábio De Souza Fernandes, Ommidala Pattawong, Darlene Q. Tan, James C. Fettinger, Paul Ha Yeon Cheong, Jared T. Shaw

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

2-Piperidinones are synthesized in a single step from imines and 2-cyano glutaric anhydrides. The reaction provides the products in good diastereoselectivity and generates a quaternary stereogenic center. Substitutions on the anhydride skeleton are well tolerated to provide 2-piperidinones with three stereogenic centers from a single transformation. The pertinent transition structures have also been computed using quantum mechanics and reveal the key interactions controlling the stereochemical outcome of the reaction.

Original languageEnglish (US)
Pages (from-to)4794-4801
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number14
DOIs
Publication statusPublished - Mar 24 2016

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Keywords

  • alkaloids
  • anhydrides
  • imine
  • lactams
  • Mannich reaction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Di Maso, M. J., Snyder, K. M., De Souza Fernandes, F., Pattawong, O., Tan, D. Q., Fettinger, J. C., ... Shaw, J. T. (2016). Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides. Chemistry - A European Journal, 22(14), 4794-4801. https://doi.org/10.1002/chem.201504424