Synlett 2007(11): 1739-1741  
DOI: 10.1055/s-2007-982566
LETTER
© Georg Thieme Verlag Stuttgart · New York

Enantio- and Diastereoselective Hydrogenation of a Fluorinated Diketone

Matthew L. Clarke*b, Marcia B. France*a, Fergus R. Knightb, Jamie J. R. Frewb, Geoffrey J. Roffb
a Department of Chemistry, Washington and Lee University, Lexington, VA 24450, USA
b School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
Fax: +44(1334)463808; e-Mail: mc28@st-andrews.ac.uk;
Further Information

Publication History

Received 19 December 2006
Publication Date:
25 June 2007 (online)

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Abstract

Asymmetric hydrogenation of dibenzoyl-difluoro­methane has been studied for the first time. In contrast to ­BINAL-H, baker’s yeast and CBS reduction procedures, ruthenium-catalysed hydrogenation using axially chiral diphosphine ligands provides excellent yield, diastereoselectivity and good enantioselectivity (up to 72% ee). Enantiomer enrichment by recrystallisation allows for the pure fluorinated diol to be isolated as a single enantiomer in moderate yield.