Michelet, Véronique and Charruault, Lise and Gladiali, Serafino Gabriele and Genêt, Jean-Pierre (2006) Alkoxy- and hydroxycyclization of enynes catalyzed by Pd(II) and Pt(II) catalysts. Pure and Applied Chemistry, Vol. 78 (2), p. 397-407. eISSN 1365-3075. Article.
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.
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