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Dimethylzinc-Mediated Alkynylation of Imines

Lorenzo Zani, Silvia Alesi, Pier Giorgio Cozzi and Carsten Bolm*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany, Email:

L. Zani, S. Alesi, P. G. Cozzi, C. Bolm, J. Org. Chem., 2006, 71, 1558-1562.

DOI: 10.1021/jo052273o

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Treatment of various aromatic and aliphatic aldimines with a mixture of a terminal alkynes and dimethylzinc solution in toluene yields the corresponding protected propargylic amines in moderate to excellent yields. A three-component synthesis of propargylic amines with an aldehyde, ortho-methoxyaniline and phenylacetylene through in situ formation of the corresponding imine in the presence of dimethylzinc was developed.

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Key Words

Propargylamines, Multicomponent Reactions

ID: J42-Y2006-410