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Issue 16, 2013
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Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich–hydroamination reactions†

Alexandre Jean,ab   Jérôme Blanchet,*a   Jacques Rouden,a   Jacques Maddalunob  and  Michaël De Paolis*b  
Author affiliations

* Corresponding authors

a 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

Abstract

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.

Graphical abstract: Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich–hydroamination reactions

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Article information

https://doi.org/10.1039/C2CC38954A
Submitted
14 Dec 2012
Accepted
01 Jan 2013
First published
03 Jan 2013
Chem. Commun., 2013,49, 1651-1653
Article type
Communication
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Stereoselective access to heteroarylmethylene-substituted pyrrolidines: fully organocatalytic Mannich–hydroamination reactions

A. Jean, J. Blanchet, J. Rouden, J. Maddaluno and M. De Paolis, Chem. Commun., 2013, 49, 1651
DOI: 10.1039/C2CC38954A

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