6456-85-5Relevant academic research and scientific papers
Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides
Di Maso, Michael J.,Snyder, Kevin M.,De Souza Fernandes, Fábio,Pattawong, Ommidala,Tan, Darlene Q.,Fettinger, James C.,Cheong, Paul Ha-Yeon,Shaw, Jared T.
, p. 4794 - 4801 (2016/04/05)
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.
