A General Aminocatalytic Method for the Synthesis of Aldimines
Sara Morales, Fernando G. Guijarro, José Luis García Ruano* and M. Belén Cid*
*Department of Organic Chemistry, Universidad Autónoma de
Madrid, Cantoblanco 28049, Madrid, Spain, Email: belen.cid
uam.es,
joseluis.garcia.ruanouam.es
S. Morales, F. G. Guijarro, J. L. G. Ruano, M. B. Cid, J. Am. Chem. Soc., 2014, 136, 1082-1089.
DOI: 10.1021/ja4111418
Abstract
Pyrrolidine as an organocatalyst enables a general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing an amino group. This nucleophilic catalysis proceeds via iminium activation with outstanding yields in the absence of acids and metals under simple conditions. The method has been applied to the synthesis of N-sulfinyl, N-sulfonyl imines, N-phosphinoyl, N-alkyl, and N-aryl imines.
see article for more examples
proposed mechanism
Key Words
imines, N-sulfinyl imines, N-sulfonyl imines, organocatalysis
ID: J48-Y2014
