title: Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides.
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.
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA.
authors.forename: Michael J
authors.identifier: http://orcid.org/0000-0003-1262-6126
authors.initials: MJ
authors.lastname: Di Maso
authors.affiliation: Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA.
authors.forename: Kevin M
authors.identifier: http://orcid.org/0000-0003-3029-4815
authors.initials: KM
authors.lastname: Snyder
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA.|Department of Chemistry, Federal University of Juiz de Fora, Campus Martelos, Juiz de Fora, MG 36036-330, Brazil.
authors.forename: Fábio
authors.initials: F
authors.lastname: De Souza Fernandes
authors.affiliation: Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA.
authors.forename: Ommidala
authors.initials: O
authors.lastname: Pattawong
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA.
authors.forename: Darlene Q
authors.initials: DQ
authors.lastname: Tan
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA.
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.affiliation: Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA.
authors.forename: Paul Ha-Yeon
authors.identifier: http://orcid.org/0000-0002-6600-2266
authors.initials: PH
authors.lastname: Cheong
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA. jtshaw@ucdavis.edu.
authors.forename: Jared T
authors.identifier: http://orcid.org/0000-0001-5190-493X
authors.initials: JT
authors.lastname: Shaw
keywords: Mannich reaction; alkaloids; anhydrides; imine; lactams