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

作者:Di Maso Michael J; Snyder Kevin M; Fernandes Fabio De Souza; Pattawong Ommidala; Tan Darlene Q; Fettinger James C; Cheong Paul Ha Yeon*; Shaw Jared T*
来源:Chemistry - A European Journal, 2016, 22(14): 4794-4801.
DOI:10.1002/chem.201504424

摘要

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.

  • 出版日期2016-3-24