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

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.

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DOI: 10.1351/pac200678020397

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.

Item Type:Article
ID Code:844
Status:Published
Refereed:Yes
Uncontrolled Keywords:Asymmetric catalysis, atom economy, cycloisomerization, palladium, platinum
Subjects:Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:International Union of Pure and Applied Chemistry
eISSN:1365-3075
Publisher Policy:Depositato in conformità con la politica di copyright dell'Editore
Deposited On:18 Aug 2009 10:03

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