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

Autor: Di Maso MJ; Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA., Snyder KM; Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA., De Souza Fernandes F; 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., Pattawong O; Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA., Tan DQ; Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA., Fettinger JC; Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA., Cheong PH; Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA., Shaw JT; Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA, 95616, USA. jtshaw@ucdavis.edu.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2016 Mar 24; Vol. 22 (14), pp. 4794-801. Date of Electronic Publication: 2016 Mar 01.
DOI: 10.1002/chem.201504424
Abstrakt: 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.)
Databáze: MEDLINE
Externí odkaz: