A new class of well-defined ruthenium catalysts for enantioselective transfer hydrogenation of various ketones

Kayan C., Meric N., RAFIKOVA K., ZAZYBIN A., GÜRBÜZ N., Karakaplan M., ...Daha Fazla

JOURNAL OF ORGANOMETALLIC CHEMISTRY, cilt.869, ss.37-47, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 869
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.jorganchem.2018.06.002
  • Dergi Adı: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.37-47
  • Anahtar Kelimeler: Asymmetric transfer hydrogenation, Chiral ruthenium complexes, Phosphinites, Epoxide ring opening, Homogeneous catalysis, ASYMMETRIC TRANSFER HYDROGENATION, HIGHLY EFFICIENT CATALYSTS, CROSS-COUPLING REACTIONS, DIELS-ALDER REACTIONS, AROMATIC KETONES, PHOSPHINITE LIGANDS, CRYSTAL-STRUCTURE, METAL-COMPLEXES, AMINO-ALCOHOLS, CHIRAL LIGANDS
  • İnönü Üniversitesi Adresli: Evet

Özet

A pair of novel optically pure phosphinite ligands were synthesized by ring opening reaction of chiral amines with (R)-styrene oxide or (S)-glycidyl phenyl ether oxide using a straightforward method in high yields and their ruthenium complexes were described in detail. The ruthenium complexes proved to be highly efficient catalysts for the enantioselective hydrogenation of ketones, affording products up to 99% ee. The results showed that the corresponding chiral alcohols could be obtained with high activity and excellent enantioselectivities at the desired temperature. (2S)-1-{benzyl[(1S)-1-(naphthalen-1-yl)ethyl]amino}-3-phenoxypropan-2-yl diphenylphosphinito[dichloro(eta(6)-benzene)ruthenium (II)] acts an excellent catalyst in the reduction of ketones, giving the corresponding alcohol up to 99% ee. (C) 2018 Elsevier B.V. All rights reserved.