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Issue 1, 2016
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Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles

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Abstract

The generation of cyclopent-2-enylzinc from cyclopentadiene based on a titanium-catalyzed hydroalumination/transmetallation sequence is described. Applied to the allylmetallation of phenylglycinol-derived imines, this sequence leads to homoallylic amines with moderate to good stereoselectivities. The synthesis of disubstituted azetidines and piperidines illustrates the potential of the method.

Graphical abstract: Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles

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Article information


Submitted
22 Oct 2015
Accepted
05 Nov 2015
First published
05 Nov 2015

Org. Biomol. Chem., 2016,14, 69-73
Article type
Communication

Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles

M. Coffinet, S. Lamy, F. Jaroschik and J. Vasse, Org. Biomol. Chem., 2016, 14, 69
DOI: 10.1039/C5OB02184G

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