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Paper | Regular issue | Vol 63, No. 5, 2004, pp.1027-1044
Published online, 24th February, 2004
DOI: 10.3987/COM-03-9978
Palladium-catalyzed Cyclocarbonylation of Unsaturated Alcohols and Amines. Chemoselective Synthesis of Heterocycle-substituted γ- and δ-Lactones and Lactams

Catia Granito, Luigino Troisi,* and Ludovico Ronzini

*Department of Sciences and Biological and Environmental Technologies, University of Lecce, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy

Abstract

Unsaturated alcohols and amines react with carbon monoxide and hydrogen, in the presence of a catalytic amount of palladium acetate and a phosphine ligand, to afford selectively heterocycle-substituted γ- and δ-lactones and lactams. The distribution of five- and six-membered ring compounds can be modulated by an appropriate combination of solvent and phosphine ligand. The five-membered products are formed in two isomeric forms trans and cis with a modest diasteroselectivity (trans>cis).