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Polymer‐Supported Chiral 1,2‐Diamines by Radical Copolymerization with Vinyl Monomer for Asymmetric Hydrogenation of Aromatic Ketones
Author(s) -
Haraguchi Naoki,
Chiba Masahiro,
Takahashi Miyuki,
Itsuno Shinichi
Publication year - 2007
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200750405
Subject(s) - polymer chemistry , copolymer , acetophenone , monomer , moiety , diamine , acrylate , methacrylate , methyl methacrylate , catalysis , chemistry , binap , polymer , isopropyl , organic chemistry , enantioselective synthesis
Novel polymer‐supported chiral 1,2‐diamines have successfully synthesized by radical copolymerization of N ‐Boc protected enantiopure 1,2‐diamine bearing two vinylphenyl moieties (( S , S )‐ 5 ) with various achiral vinyl monomer including methyl methacrylate, 2‐hydroxyethyl methacrylate, butyl acrylate, and N ‐isopropyl acrylamide, followed by deprotection of N ‐Boc moiety. Hydrogenation of acetophenone in 2‐propanol/DMF mixed solvent was performed with use of polymeric catalyst system prepared from the polymer‐supported chiral 1,2‐diamine and RuCl 2 /( S )‐BINAP. The reaction proceeded smoothly to give 1‐phenylethanol in quantitative yield with high level of enantioselectivity. In addition, various other aromatic ketones could be asymmetrically hydrogenated by the polymeric catalyst system. Furthermore, the polymeric catalyst could be reused several times in hydrogenation of aromatic ketones without loss of the enantioselectivity.