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

10 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
StatePublished - Mar 24 2016

Keywords

  • alkaloids
  • anhydrides
  • imine
  • lactams
  • Mannich reaction

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides'. Together they form a unique fingerprint.

  • Cite this

    Di Maso, M. J., Snyder, K. M., De Souza Fernandes, F., Pattawong, O., Tan, D. Q., Fettinger, J. C., Cheong, P. H. Y., & 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