Enantioselective routes to both enantiomers of aryl alcohols with a single catalyst antipode: Ru and Os transfer hydrogenation catalysts.
[reaction--see text] The kinetic resolution of secondary aryl alcohols has been investigated. When (CyRuCl(2))(2), (1R,2S)-(+)-cis-1-amino-2-indanol, and KOH or (t)BuOK (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 (CyOsCl(2))(2), (1R,2S)-(+)-cis-1-amino-2-indanol, and (t)BuOK, yielding ee's of up to 98% (S).
Faller
J W
JW
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA. jack.faller@yale.edu
Lavoie
A R
AR
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D009992:Osmium; D012428:Ruthenium; D013237:Stereoisomerism
D000438:Alcohols; D009992:Osmium; D012428:Ruthenium