Enantioselective routes to both enantiomers of aryl alcohols with a single catalyst antipode: Ru and Os transfer hydrogenation catalysts

[GRAPHICS] The kinetic resolution of secondary aryl alcohols has been investigated. When (CyRuCl2)(2), (1R,2S)-(+)-cis-1-amino-2-indanol, and KOH or (BuOK)-Bu-t (catalyst 1) were combined in the presence of (+/-)-alcohols, ee's > 90% were generally observed. When applied to the kinetic resolution of (+/-)-indanol and (+/-)-tetralol, ee's = 99% (R) were observed. In addition, the asymmetric transfer hydrogenation of ketones was investigated with a catalyst, 2, generated in situ from (Cy0sCL(2))(2), (1R,2S)-(+)-cis-1-amino-2-indanol, and (BuOK)-Bu-t, yielding ee's of up to 98% (S).