M. Hennig, Kurt Püntener, M. Scalone
May 19, 2000
Citations
1
Influential Citations
51
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The first synthesis of (R)- and (S)-4-hydroxyisophorone by catalytic transfer hydrogenation of ketoisophorone is reported. Ruthenium catalysts containing commercially available chiral amino alcohols afforded 4-hydroxyisophorone in up to 97% selectivity and 97% ee. (R)- or (S)-4-Hydroxyisophorones with >99% ee were isolated by crystallization. The catalyst precursors [RuCl2((S,R)-ADPE)(η6-p-cymene)] ((S,R)-ADPE=(1S,2R)-amino-1,2-diphenylethanol-N) and (RRu)-[RuCl((S,R)-ADPE−1)(η6-p-cymene)] (ADPE−1=amino-1,2-diphenylethanolato-N,O) were isolated for the first time and the X-ray crystal structure of the latter determined.