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Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen, CNRS UMR, 6 boulevard du Marechal Juin, 14050 Caen, France
E-mail: jerome.blanchet@ensicaen.fr
b
Laboratoire des Fonctions Azotées et Oxygénées Complexes de l'IRCOF, CNRS UMR 6014 & FR 3038, Université et INSA de Rouen, Mont Saint-Aignan, France
E-mail: michael.depaolis@univ-rouen.fr
Chem. Commun., 2013,49, 1651-1653
DOI:
10.1039/C2CC38954A
Received
14 Dec 2012,
Accepted
01 Jan 2013
First published online
03 Jan 2013
A one-pot sequence of organocatalytic transformations delivers heteroarylmethylene-substituted pyrrolidines with high stereo- and enantioselectivity. A Mannich coupling of N-heteroarylalkyne aldehydes with aldimine and an original metal-free hydroamination of the resulting adducts are the key transformations of the process delivering highly functionalized molecules with high potential for synthetic applications.