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Di Maso MJ, Snyder KM, De Souza Fernandes F, et al. Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides. Chemistry. 2016;22(14):4794-801doi: 10.1002/chem.201504424.
Di Maso, M. J., Snyder, K. M., De Souza Fernandes, F., Pattawong, O., Tan, D. Q., Fettinger, J. C., Cheong, P. H., & Shaw, J. T. (2016). Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides. Chemistry (Weinheim an der Bergstrasse, Germany), 22(14), 4794-801. https://doi.org/10.1002/chem.201504424
Di Maso, Michael J, et al. "Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,14 (2016): 4794-801. doi: https://doi.org/10.1002/chem.201504424
Di Maso MJ, Snyder KM, De Souza Fernandes F, Pattawong O, Tan DQ, Fettinger JC, Cheong PH, Shaw JT. Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides. Chemistry. 2016 Mar 24;22(14):4794-801. doi: 10.1002/chem.201504424. Epub 2016 Mar 01. PMID: 26929008.
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Chemistry. 2016 Mar 24;22(14):4794-801. doi: 10.1002/chem.201504424. Epub 2016 Mar 01.

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

Chemistry (Weinheim an der Bergstrasse, Germany)

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

Affiliations

  1. Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA.
  2. Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA.
  3. Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, MG 36036-330, Brazil.
  4. Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA. [email protected].

PMID: 26929008 DOI: 10.1002/chem.201504424

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.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Mannich reaction; alkaloids; anhydrides; imine; lactams

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