Synthesis 2007(24): 3877-3885  
DOI: 10.1055/s-2007-990917
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Paracyclophane Phosphine for Highly Enantioselective Ruthenium-Catalyzed Hydrogenation of Prochiral Ketones

Murthy N. Cheemalaa, Maud Gayralb, John M. Brownb, Kai Rossenc, Paul Knochel*a
a Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 München, Germany
b Chemical Research Laboratory, 12 Mansfield Rd, Oxford, OX1 3TA, UK
c Sanofi-Aventis, G 838, Industriepark Höchst, 65926 Frankfurt am Main, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 21 August 2007
Publication Date:
28 November 2007 (online)

Abstract

The synthesis of a new paracyclophane phosphine is described. This ligand was highly efficient in the ruthenium-catalyzed asymmetric hydrogenation of various aromatic and heteroaromatic ketones.

15

We used only the two diamines (R,R)-DPEN and (S,S)-DPEN; DPEN = 1,2-diphenylethylenediamine. Complex 6a was prepared by use of the (R,R)-amine, whereas the (S,S)-diamine was used for complex 6b.