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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.ciduam.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 (free Supporting Information)


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.

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proposed mechanism



Key Words

imines, N-sulfinyl imines, N-sulfonyl imines, organocatalysis


ID: J48-Y2014