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Furanoside phosphite–phosphoroamidite and diphosphoroamidite ligands applied to asymmetric Cu-catalyzed allylic substitution reactions

Authors
Magre, Marc
Mazuela, Javier
Diéguez, Montserrat
Pàmies, Oscar
Published in Tetrahedron: Asymmetry. 2012, vol. 23, no. 1, p. 67-71
Abstract A phosphite–phosphoroamidite and diphosphoroamidite ligand library was applied in the Cu-catalyzed allylic substitution of a range of cinnamyl-type substrates using several organometallic nucleophiles. Results indicated that selectivity depended strongly on the ligand parameters (position of the phosphoroamidite group at either C-5 or C-3 of the furanoside backbone, as well as the configuration of C-3, the introduction of a second phosphoroamidite moiety, the substituents and configurations in the biaryl phosphite/phosphoroamidite moieties), the nature of the leaving group of the substrate and the alkylating reagent. Good enantioselectivities (up to 76%) and activity combined with high regioselectivities were obtained.
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MAGRE, Marc et al. Furanoside phosphite–phosphoroamidite and diphosphoroamidite ligands applied to asymmetric Cu-catalyzed allylic substitution reactions. In: Tetrahedron: Asymmetry, 2012, vol. 23, n° 1, p. 67-71. https://archive-ouverte.unige.ch/unige:18837

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Deposited on : 2012-03-16

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