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Article

Dimethylzinc-Mediated Alkynylation of Imines

Supporting Info

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

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany, and Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum, Universit di Bologna, Via Selmi 2, I-40126 Bologna, Italy

J. Org. Chem., 2006, 71 (4), pp 1558–1562

DOI: 10.1021/jo052273o

Publication Date (Web): January 20, 2006

†

RWTH Aachen University.

‡

Università di Bologna.

To whom correspondence should be addressed. Fax: +49-241-8092391. Phone: +49-241-8094675.

, carsten.bolm@oc.rwth-aachen.de

Abstract

The treatment of various aromatic and aliphatic aldimines with a mixture of a terminal alkyne and a commercially available dimethylzinc solution in toluene yields the corresponding protected propargylic amines in moderate to excellent yields. The reaction proceeds in the absence of any activator. These observations led to the development of a three-component synthesis of propargylic amines in which the product was obtained upon mixing an aldehyde with ortho-methoxyaniline and phenylacetylene in the presence of dimethylzinc, through in situ formation of the corresponding imine.

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Published In Issue February 17, 2006
Received November 2, 2005

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Article

Dimethylzinc-Mediated Alkynylation of Imines