Synthesis of Novel Polymers with a Chiral 1,2-Diamine Moiety by Polycondensation and their Application to Catalyst for Asymmetric Hydrogenation of Aromatic Ketones |
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Authors: | Naoki Haraguchi Nilesh anand Prasad Takao Uchiyama Shinichi Itsuno |
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Affiliation: | Department of Materials Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tenpaku-cho, Toyohashi, Aichi 441-8580, Japan |
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Abstract: | Summary: Novel polymers with chiral 1,2-diamine moiety were successfully synthesized by polycondensation of N-Boc protected enantiopure 1,2-diamine bearing two phenol groups ( S , S )-4 , bisphenol derivatives, and dibromides, followed by deprotection of N-Boc moiety. Hydrogenation of acetophenone was performed with use of polymeric catalyst system prepared from the polymer-supported chiral 1,2-diamine and RuCl2/(S)-BINAP. The reaction proceeded smoothly even in 2-propanol to give 1-phenylethanol in quantitative yield with high level of enantioselectivity. Furthermore, various other aromatic ketones could be asymmetrically hydrogenated by the polymeric catalyst system. |
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Keywords: | catalysts chiral metal-polymer complexes polycondensation supports |
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