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Synthesis of chiral monodentate binaphthophosphepine ligands and their application in asymmetric hydrogenations

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
15
Issue
17
Identifiers
DOI: 10.1016/j.tetasy.2004.07.022

Abstract

Abstract A general synthesis of chiral monodentate 4,5-dihydro-3 H-dinaphthophosphepines 4 and a detailed study of the catalytic performance of the resulting ligands 4a– n in benchmark hydrogenation reactions is presented. Hydrogenation of methyl α-acetamidocinnamate 11 and methyl α-acetamidoacrylate 13 proceeded with enantioselectivities up to 95% and 94%, respectively. The best enantioselectivity for the rhodium-catalyzed hydrogenation of dimethyl itaconate 15 was 88%.

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