Oxidative Kinetic Resolution of Racemic Alcohols Catalyzed by Chiral Ferrocenyloxazolinylphosphine−Ruthenium Complexes

• DOI: 10.1021/jo0345087
• Publication Date: 2003-07-18T04:48:49Z
• Authors: Yoshiaki Nishibay...; Akiyoshi Yamauchi; Gen Onodera; Sakae Uemura
• Keywords: Kinetic resolution; Enantiomeric excess; Racemic mixture; Oxidative addition

Oxidative kinetic resolution of racemic secondary alcohols by using acetone as a hydrogen acceptor in the presence catalytic amount [RuCl2(PPh3)(ferrocenyloxazolinylphosphine)] (2) proceeds effectively to recover corresponding high yields with an excellent enantioselectivity. When 1-indanol is employed alcohol, oxidation quite smoothly even 0.0025 mol % catalyst 2 give optically active good yield enantioselectivity (up 94% ee), where turnover frequency (TOF) exceeds 80 000 h-1. From practical viewpoint, investigated large scale, pure (S)-1-indanol (75 g, 56% yield, >99% ee) being obtained from (134 g) employing this method twice.