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

Kathrin Junge, Bernhard Hagemann, Stephan Enthaler, Anke Spannenberg, Manfred Michalik, Günther Oehme, Axel Monsees, Thomas Riermeier, Matthias Beller

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

A general synthesis of chiral monodentate 4,5-dihydro-3H- 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%.

Original languageEnglish
Pages (from-to)2621-2631
Number of pages11
JournalTetrahedron Asymmetry
Volume15
Issue number17
DOIs
StatePublished - 6 Sep 2004
Externally publishedYes

Fingerprint

Dive into the research topics of 'Synthesis of chiral monodentate binaphthophosphepine ligands and their application in asymmetric hydrogenations'. Together they form a unique fingerprint.

Cite this