Issue 9, 2013
From the journal:

Chemical Communications

Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes†

Marie S. T. Morin,a   Sara Alya  and  Bruce A. Arndtsen*a  

* Corresponding authors

a Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC H3A 0B8, Canada
E-mail: bruce.arndtsen@mcgill.ca

Abstract

2-Pyrrolines can be generated by the PhP(2-catechyl) mediated coupling of alkene-tethered imines and acid chlorides. This reaction proceeds via phosphorus-containing 1,3-dipoles, which undergo cycloaddition with alkenes with high stereo- and regioselectivity. The modularity of this reaction can be used to assemble a range of polysubstituted pyrrolines in one pot transformations.

Graphical abstract: Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes

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Article information

DOI
https://doi.org/10.1039/C2CC38274A
Article type
Communication
Submitted
16 Nov 2012
Accepted
05 Dec 2012
First published
06 Dec 2012

Chem. Commun., 2013,49, 883-885

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Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes

M. S. T. Morin, S. Aly and B. A. Arndtsen, Chem. Commun., 2013, 49, 883 DOI: 10.1039/C2CC38274A

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