New chiral ruthenium(II)–phosphinite complexes containing a ferrocenyl group in enantioselective transfer hydrogenations of aromatic ketones

A new and versatile class of unsymmetrical ferrocenyl-phosphinite ligands possessing a stereogenic center has been prepared from commercially available, inexpensive aminoacids such as, d-, l-phenylglycine and d-, l-phenylalanine, through a concise synthetic procedure. These ligands are not very sens...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2013-10, Vol.24 (20), p.1257-1264
Main Authors: Ak, Bünyamin, Elma, Duygu, Meriç, Nermin, Kayan, Cezmi, Işık, Uğur, Aydemir, Murat, Durap, Feyyaz, Baysal, Akın
Format: Article
Language:English
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Summary:A new and versatile class of unsymmetrical ferrocenyl-phosphinite ligands possessing a stereogenic center has been prepared from commercially available, inexpensive aminoacids such as, d-, l-phenylglycine and d-, l-phenylalanine, through a concise synthetic procedure. These ligands are not very sensitive to air and moisture, and display good enantioselectivities in the ruthenium-catalyzed asymmetric transfer hydrogenation of acetophenone derivatives, in which up to 91% ee was obtained. A comparison of the catalytic properties of amino alcohols and other analogues based on a ferrocenyl backbone is also discussed briefly. The structures of these ligands and their corresponding complexes have been elucidated by a combination of multinuclear NMR spectroscopy, IR spectroscopy, and elemental analysis.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2013.09.004