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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 397-407

Alkoxy- and hydroxycyclization of enynes catalyzed by Pd(II) and Pt(II) catalysts

Véronique Michelet1, Lise Charruault1, Serafino Gladiali2 and Jean-Pierre Genêt1

1 Laboratoire de Synthèse Sélective Organique et Produits Naturels, ENSCP, 11 rue P. et M. Curie, F-75231 Paris Cédex 05, France
2 Dipartimento di Chimica, Università di Sassari, Via Vienna 2, 07100 Sassari, Italy

Abstract: The development of a novel reaction ideal in terms of atom economy was achieved. The scope of the reaction was evaluated in the presence of Pd and Pt catalysts. The first enantioselective Pt-promoted enyne carboalkoxycyclization was developed in up to 85 % stereoselectivity. This ideal atom-economical reaction afforded the corresponding functionalized five-membered carbo- and heterocycles in good to excellent yields. The use of silver salts combined with (R)-Ph-BINEPINE, a monophosphane atropisomeric ligand, was found to be the best-suited combination for moderate to high enantioselectivities on carbonated and nitrogenated substrates.