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Furanoside phosphite-phosphoroamidite and diphosphoroamidite ligands for Cu-catalyzed asymmetric 1,4-addition reactions

Authors
Raluy, Eva
Pàmies, Oscar
Diéguez, Montserrat
Published in Tetrahedron: Asymmetry. 2009, vol. 20, no. 16, p. 1930-1935
Abstract A sugar-based phosphite–phosphoroamidite and diphosphoroamidite ligand library L1–L5a–g was tested in the asymmetric Cu-catalyzed 1,4-conjugate addition reactions of ß-substituted and ß,ß'-disubstituted enones. Our results indicated that the selectivity was strongly dependent on the ligand parameters and on the substrate structure. Moderate-to-good enantioselectivities (ees up to 84%) were obtained in the 1,4-addition of several types of ß-substituted cyclic and linear substrates. Of particular note is the high enantioselectivity (ees up to 90%) obtained for the more challenging ß,ß'-disubstituted 3-methyl-cyclohexenone.
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RALUY, Eva et al. Furanoside phosphite-phosphoroamidite and diphosphoroamidite ligands for Cu-catalyzed asymmetric 1,4-addition reactions. In: Tetrahedron: Asymmetry, 2009, vol. 20, n° 16, p. 1930-1935. https://archive-ouverte.unige.ch/unige:8106

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Deposited on : 2010-06-21

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