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Palladium-Catalyzed Addition of Alkynes to Cyclopropenes: An Entry to Stereodefined Alkynylcyclopropanes

Alphonse Tenaglia*, Karel Le Jeune, Laurent Giordano and Gerard Buono

*Aix-Marseille Universite, ECM-UMR 6263, ISM2, Av. Escadrille Normandie-Niemen, 13397 Marseille cedex 20, France, Email: alphonse.tenagliauniv-cezanne.fr

A. Tenaglia, K. Le Jeune, L. Giordano, G. Buono, Org. Lett., 2011, 13, 636-639.

DOI: 10.1021/ol1028833 (free Supporting Information)


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Abstract

A highly diastereoselective addition of terminal alkynes to unsymmetrical gem-disubstituted cyclopropenes to give alkynylcyclopropanes in good to excellent yields is catalyzed by the Herrmann-Beller phosphapalladacycle. The stereofacial discrimination at the approach of the bulky alkynylpalladium species is believed to be responsible for the diastereoselectivity control of the addition reaction.

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Key Words

Cyclopropylation, Alkynylation


ID: J54-Y2011-0340