Synthesis of polymers containing chiral 1,2-diamine derivatives and their application to asymmetric reactions

Itsuno, Shinichi; Takahashi, Miyuki; Arakawa, Yukihiro; Haraguchi, Naoki

doi:10.1351/pac200779091471

Pure Appl. Chem., 2007, Vol. 79, No. 9, pp. 1471-1479

http://dx.doi.org/10.1351/pac200779091471

Synthesis of polymers containing chiral 1,2-diamine derivatives and their application to asymmetric reactions

Shinichi Itsuno, Miyuki Takahashi, Yukihiro Arakawa and Naoki Haraguchi

Department of Materials Science, Toyohashi University of Technology, Tempaku-cho, Toyohashi 441-8580, Japan

Abstract: Polymer-supported chiral 1,2-diamine derivatives have been prepared. The polymers containing free 1,2-diamine moiety were applied to enantioselective hydrogenation catalyst by combination with RuCl₂-BINAP complex. Asymmetric hydrogenation of aromatic ketones was performed by means of the polymeric catalyst derived from these polymers to give the chiral secondary alcohols with high ee in quantitative conversion. The polymers containing 1,2-diamine monosulfonamide were applied to enantioselective transfer hydrogenation catalyst by combination with RuCl₂-p-cymene complex. Asymmetric transfer hydrogenation of aromatic ketones was performed by means of the polymeric catalyst to afford the chiral secondary alcohols. A high level of enantioselectivities up to 99 % ee was attained in neat water by using the polymeric catalyst prepared from quaternary ammonium salt-type polymer support.