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.
Alkoxy- and hydroxycyclization of enynes catalyzed by Pd(II) and Pt(II) catalysts / Michelet, Véronique; Charruault, Lise; Genêt, Jean-Pierre; Gladiali, Serafino Gabriele. - 78:2(2006), pp. 397-407. [10.1351/pac200678020397]
Alkoxy- and hydroxycyclization of enynes catalyzed by Pd(II) and Pt(II) catalysts
Gladiali, Serafino Gabriele
2006-01-01
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.| File | Dimensione | Formato | |
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